#------------------------------------------------------------------------------
#$Date: 2025-11-29 22:41:41 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303867 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/40/7064035.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_7064035
loop_
_publ_author_name
'Price, Lee'
'Li, Zonyuan'
'Zhang, Wei'
_publ_section_title
;
 Synthesis of a pyrroloquinoline-containing polycyclic scaffold via
 decarboxylative [3+2] cycloaddition and aza-Wittig reactions
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18970
_journal_page_last               18973
_journal_paper_doi               10.1039/D5NJ03128A
_journal_volume                  49
_journal_year                    2025
_chemical_formula_sum            'C14 H15 N3 O'
_chemical_formula_weight         241.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   'Fourier difference maps'
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2025-05-13 deposited with the CCDC.	2025-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.768(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1162(7)
_cell_length_b                   11.1065(9)
_cell_length_c                   10.7813(8)
_cell_measurement_reflns_used    8604
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.75
_cell_volume                     1190.01(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-IV photon 200'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14404
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_min         3.062
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.340
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0358
_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)+(0.0484P)²+0.3207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2126
_reflns_number_total             2441
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj03128a2.cif
_cod_data_source_block           umd2959d_a
_cod_depositor_comments
'Adding full bibliography for 7064031--7064035.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7064035
_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   0.967
_shelx_estimated_absorpt_t_max   0.971
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51860(12) 0.21462(11) 0.82413(10) 0.0631(3) Uani 1 1 d . . . . .
N1 N 0.33351(11) 0.55809(9) 0.69784(9) 0.0373(3) Uani 1 1 d . . . . .
N2 N 0.45453(10) 0.26564(9) 0.61528(10) 0.0377(3) Uani 1 1 d . . . . .
N3 N 0.38014(10) 0.39112(9) 0.44097(9) 0.0343(2) Uani 1 1 d . . . . .
C1 C 0.36380(14) 0.47375(13) 0.80611(12) 0.0433(3) Uani 1 1 d . . . . .
H1A H 0.4605 0.4756 0.8410 0.052 Uiso 1 1 calc R U . . .
C2 C 0.32316(13) 0.34457(12) 0.75387(12) 0.0415(3) Uani 1 1 d . . . . .
H2A H 0.2633 0.3044 0.8026 0.050 Uiso 1 1 calc R U . . .
C3 C 0.44242(13) 0.26636(12) 0.74094(13) 0.0430(3) Uani 1 1 d . . . . .
C4 C 0.36338(11) 0.34352(10) 0.54467(11) 0.0326(3) Uani 1 1 d . . . . .
C5 C 0.28538(11) 0.48276(11) 0.39500(11) 0.0330(3) Uani 1 1 d . . . . .
C6 C 0.27332(13) 0.51805(13) 0.26977(12) 0.0411(3) Uani 1 1 d . . . . .
H6A H 0.3243 0.4797 0.2181 0.049 Uiso 1 1 calc R U . . .
C7 C 0.18654(14) 0.60934(14) 0.22125(13) 0.0478(3) Uani 1 1 d . . . . .
H7A H 0.1796 0.6323 0.1373 0.057 Uiso 1 1 calc R U . . .
C8 C 0.10955(14) 0.66713(13) 0.29687(13) 0.0465(3) Uani 1 1 d . . . . .
H8A H 0.0502 0.7280 0.2637 0.056 Uiso 1 1 calc R U . . .
C9 C 0.12180(12) 0.63345(12) 0.42251(12) 0.0390(3) Uani 1 1 d . . . . .
H9A H 0.0705 0.6724 0.4735 0.047 Uiso 1 1 calc R U . . .
C10 C 0.20962(11) 0.54239(10) 0.47307(11) 0.0322(3) Uani 1 1 d . . . . .
C11 C 0.22147(12) 0.50211(11) 0.60806(11) 0.0335(3) Uani 1 1 d . . . . .
H11A H 0.1364 0.5174 0.6363 0.040 Uiso 1 1 calc R U . . .
C12 C 0.25325(12) 0.36832(11) 0.61809(12) 0.0356(3) Uani 1 1 d . . . . .
H12A H 0.1737 0.3177 0.5916 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2857(2) 0.50837(17) 0.90843(15) 0.0675(5) Uani 1 1 d . . . . .
H13A H 0.3035 0.4510 0.9761 0.101 Uiso 1 1 calc R U . . .
H13B H 0.1911 0.5089 0.8737 0.101 Uiso 1 1 calc R U . . .
H13C H 0.3130 0.5871 0.9401 0.101 Uiso 1 1 calc R U . . .
C14 C 0.56581(13) 0.20877(13) 0.57020(14) 0.0448(3) Uani 1 1 d . . . . .
H14A H 0.5545 0.2188 0.4804 0.067 Uiso 0.5 1 calc R U P . .
H14B H 0.6488 0.2454 0.6102 0.067 Uiso 0.5 1 calc R U P . .
H14C H 0.5677 0.1245 0.5902 0.067 Uiso 0.5 1 calc R U P . .
H14D H 0.6262 0.1736 0.6401 0.067 Uiso 0.5 1 calc R U P . .
H14E H 0.5319 0.1471 0.5103 0.067 Uiso 0.5 1 calc R U P . .
H14F H 0.6130 0.2680 0.5304 0.067 Uiso 0.5 1 calc R U P . .
H1 H 0.4077(16) 0.5618(13) 0.6589(14) 0.045(4) Uiso 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 105.62(10) . . ?
C1 N1 H1 108.6(9) . . ?
C11 N1 H1 108.0(9) . . ?
C3 N2 C4 111.30(10) . . ?
C3 N2 C14 123.14(11) . . ?
C4 N2 C14 124.51(11) . . ?
C4 N3 C5 114.23(10) . . ?
N1 C1 C13 110.61(12) . . ?
N1 C1 C2 107.06(10) . . ?
C13 C1 C2 110.78(12) . . ?
N1 C1 H1A 109.4 . . ?
C13 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C3 C2 C12 104.21(11) . . ?
C3 C2 C1 113.46(11) . . ?
C12 C2 C1 103.30(10) . . ?
C3 C2 H2A 111.8 . . ?
C12 C2 H2A 111.8 . . ?
C1 C2 H2A 111.8 . . ?
O1 C3 N2 124.16(13) . . ?
O1 C3 C2 127.67(13) . . ?
N2 C3 C2 108.15(11) . . ?
N3 C4 N2 123.83(11) . . ?
N3 C4 C12 128.05(11) . . ?
N2 C4 C12 107.89(10) . . ?
C6 C5 C10 119.37(11) . . ?
C6 C5 N3 118.14(11) . . ?
C10 C5 N3 122.41(10) . . ?
C7 C6 C5 120.68(12) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C8 120.36(12) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C9 C8 C7 119.45(12) . . ?
C9 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C10 C9 C8 120.88(12) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C5 119.24(11) . . ?
C9 C10 C11 121.69(11) . . ?
C5 C10 C11 119.01(10) . . ?
N1 C11 C10 114.81(10) . . ?
N1 C11 C12 103.76(9) . . ?
C10 C11 C12 109.68(10) . . ?
N1 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C4 C12 C11 107.97(9) . . ?
C4 C12 C2 102.51(10) . . ?
C11 C12 C2 106.94(10) . . ?
C4 C12 H12A 112.9 . . ?
C11 C12 H12A 112.9 . . ?
C2 C12 H12A 112.9 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C14 H14D 109.5 . . ?
H14A C14 H14D 141.1 . . ?
H14B C14 H14D 56.3 . . ?
H14C C14 H14D 56.3 . . ?
N2 C14 H14E 109.5 . . ?
H14A C14 H14E 56.3 . . ?
H14B C14 H14E 141.1 . . ?
H14C C14 H14E 56.3 . . ?
H14D C14 H14E 109.5 . . ?
N2 C14 H14F 109.5 . . ?
H14A C14 H14F 56.3 . . ?
H14B C14 H14F 56.3 . . ?
H14C C14 H14F 141.1 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2126(16) . ?
N1 C1 1.4834(16) . ?
N1 C11 1.4826(15) . ?
N1 H1 0.927(16) . ?
N2 C3 1.3830(18) . ?
N2 C4 1.3841(15) . ?
N2 C14 1.4514(16) . ?
N3 C4 1.2764(16) . ?
N3 C5 1.4223(15) . ?
C1 C13 1.522(2) . ?
C1 C2 1.568(2) . ?
C1 H1A 0.9800 . ?
C2 C3 1.5140(18) . ?
C2 C12 1.5251(18) . ?
C2 H2A 0.9800 . ?
C4 C12 1.5077(16) . ?
C5 C6 1.3892(17) . ?
C5 C10 1.4055(17) . ?
C6 C7 1.379(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.386(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.3882(19) . ?
C8 H8A 0.9300 . ?
C9 C10 1.3887(17) . ?
C9 H9A 0.9300 . ?
C10 C11 1.5058(16) . ?
C11 C12 1.5199(17) . ?
C11 H11A 0.9800 . ?
C12 H12A 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 H14D 0.9600 . ?
C14 H14E 0.9600 . ?
C14 H14F 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N3 0.927(16) 2.627(16) 3.5453(15) 170.8(13) 3_666
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C13 -93.00(14) . . . . ?
C11 N1 C1 C2 27.80(13) . . . . ?
N1 C1 C2 C3 104.80(12) . . . . ?
C13 C1 C2 C3 -134.51(13) . . . . ?
N1 C1 C2 C12 -7.38(13) . . . . ?
C13 C1 C2 C12 113.30(12) . . . . ?
C4 N2 C3 O1 -172.91(13) . . . . ?
C14 N2 C3 O1 -4.2(2) . . . . ?
C4 N2 C3 C2 5.30(14) . . . . ?
C14 N2 C3 C2 174.05(11) . . . . ?
C12 C2 C3 O1 -171.36(14) . . . . ?
C1 C2 C3 O1 77.01(17) . . . . ?
C12 C2 C3 N2 10.52(13) . . . . ?
C1 C2 C3 N2 -101.11(13) . . . . ?
C5 N3 C4 N2 -170.34(10) . . . . ?
C5 N3 C4 C12 3.43(17) . . . . ?
C3 N2 C4 N3 155.47(12) . . . . ?
C14 N2 C4 N3 -13.10(19) . . . . ?
C3 N2 C4 C12 -19.38(13) . . . . ?
C14 N2 C4 C12 172.05(11) . . . . ?
C4 N3 C5 C6 -163.94(11) . . . . ?
C4 N3 C5 C10 19.45(16) . . . . ?
C10 C5 C6 C7 -1.01(19) . . . . ?
N3 C5 C6 C7 -177.73(11) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C6 C7 C8 C9 0.9(2) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C9 C10 C5 -0.91(18) . . . . ?
C8 C9 C10 C11 -178.22(12) . . . . ?
C6 C5 C10 C9 1.55(17) . . . . ?
N3 C5 C10 C9 178.12(11) . . . . ?
C6 C5 C10 C11 178.93(11) . . . . ?
N3 C5 C10 C11 -4.50(16) . . . . ?
C1 N1 C11 C10 -156.66(10) . . . . ?
C1 N1 C11 C12 -36.98(12) . . . . ?
C9 C10 C11 N1 -96.35(13) . . . . ?
C5 C10 C11 N1 86.33(13) . . . . ?
C9 C10 C11 C12 147.32(11) . . . . ?
C5 C10 C11 C12 -30.00(14) . . . . ?
N3 C4 C12 C11 -37.23(16) . . . . ?
N2 C4 C12 C11 137.34(10) . . . . ?
N3 C4 C12 C2 -149.92(12) . . . . ?
N2 C4 C12 C2 24.65(12) . . . . ?
N1 C11 C12 C4 -77.26(11) . . . . ?
C10 C11 C12 C4 45.85(12) . . . . ?
N1 C11 C12 C2 32.43(12) . . . . ?
C10 C11 C12 C2 155.54(10) . . . . ?
C3 C2 C12 C4 -20.57(12) . . . . ?
C1 C2 C12 C4 98.24(10) . . . . ?
C3 C2 C12 C11 -134.02(10) . . . . ?
C1 C2 C12 C11 -15.21(12) . . . . ?
