#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301865 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/73/7227361.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_7227361
loop_
_publ_author_name
'Zhang, Yong'
'Wei, Biao-Wen'
'Wang, Wen-Xin'
'Deng, Lei-Ling'
'Nie, Long-Jun'
'Luo, Hai-Qing'
'Fan, Xiao-Lin'
_publ_section_title
;
 Direct vinylogous oxidative cross-dehydrogenative coupling of
 4-nitroisoxazoles with N-aryl tetrahydroisoquinolines in water under air
 conditions
;
_journal_issue                   3
_journal_name_full               'RSC Adv.'
_journal_page_first              1229
_journal_paper_doi               10.1039/C6RA26126D
_journal_volume                  7
_journal_year                    2017
_chemical_formula_sum            'C20 H20 N4 O2'
_chemical_formula_weight         348.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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
_audit_update_record
;
2016-09-18 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                106.376(5)
_cell_angle_beta                 98.689(5)
_cell_angle_gamma                106.505(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3993(3)
_cell_length_b                   11.0228(5)
_cell_length_c                   13.8844(9)
_cell_measurement_reflns_used    1873
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.0651
_cell_measurement_theta_min      2.9879
_cell_volume                     872.02(9)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7525
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0504
_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)+(0.0772P)²+0.0309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1464
_reflns_number_gt                2693
_reflns_number_total             3928
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra26126d2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        872.02(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7227361
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
N1 N 0.3286(2) 0.15731(13) 0.76507(10) 0.0433(3) Uani 1 1 d .
N2 N 0.9803(3) 0.23817(17) 1.05869(14) 0.0613(4) Uani 1 1 d .
N3 N 0.7143(2) 0.48428(13) 1.06167(11) 0.0518(4) Uani 1 1 d .
N4 N 0.5516(2) 0.36537(13) 0.99874(11) 0.0487(4) Uani 1 1 d .
H4 H 0.4198 0.3602 0.9690 0.058 Uiso 1 1 calc R
C1 C 0.4048(3) 0.20193(15) 0.68577(12) 0.0418(4) Uani 1 1 d .
C2 C 0.5346(3) 0.14731(16) 0.62704(13) 0.0481(4) Uani 1 1 d .
H2 H 0.5668 0.0732 0.6353 0.058 Uiso 1 1 calc R
C3 C 0.6165(3) 0.2023(2) 0.55637(14) 0.0623(5) Uani 1 1 d .
H3 H 0.7058 0.1658 0.5186 0.075 Uiso 1 1 calc R
C4 C 0.5674(4) 0.3104(2) 0.54125(15) 0.0709(6) Uani 1 1 d .
H4A H 0.6226 0.3470 0.4936 0.085 Uiso 1 1 calc R
C5 C 0.4355(4) 0.3634(2) 0.59764(16) 0.0699(6) Uani 1 1 d .
H5 H 0.4007 0.4360 0.5876 0.084 Uiso 1 1 calc R
C6 C 0.3543(3) 0.31061(18) 0.66872(14) 0.0560(5) Uani 1 1 d .
H6 H 0.2648 0.3477 0.7059 0.067 Uiso 1 1 calc R
C7 C 0.0821(3) 0.09689(18) 0.74421(15) 0.0560(5) Uani 1 1 d .
H7A H 0.0119 0.1537 0.7199 0.067 Uiso 1 1 calc R
H7B H 0.0420 0.0923 0.8081 0.067 Uiso 1 1 calc R
C8 C -0.0067(3) -0.04329(19) 0.66366(17) 0.0619(5) Uani 1 1 d .
H8A H -0.1647 -0.0850 0.6595 0.074 Uiso 1 1 calc R
H8B H 0.0057 -0.0369 0.5964 0.074 Uiso 1 1 calc R
C9 C 0.1217(3) -0.13065(17) 0.68969(14) 0.0505(4) Uani 1 1 d .
C10 C 0.0285(3) -0.27099(18) 0.64872(15) 0.0634(5) Uani 1 1 d .
H10 H -0.1162 -0.3113 0.6053 0.076 Uiso 1 1 calc R
C11 C 0.1444(4) -0.35078(19) 0.67077(16) 0.0650(5) Uani 1 1 d .
H11 H 0.0784 -0.4440 0.6424 0.078 Uiso 1 1 calc R
C12 C 0.3587(3) -0.29315(17) 0.73494(14) 0.0580(5) Uani 1 1 d .
H12 H 0.4386 -0.3471 0.7495 0.070 Uiso 1 1 calc R
C13 C 0.4542(3) -0.15466(16) 0.77755(13) 0.0498(4) Uani 1 1 d .
H13 H 0.5984 -0.1157 0.8214 0.060 Uiso 1 1 calc R
C14 C 0.3370(3) -0.07208(15) 0.75570(12) 0.0425(4) Uani 1 1 d .
C15 C 0.4445(3) 0.07977(15) 0.80780(12) 0.0410(4) Uani 1 1 d .
H15 H 0.5981 0.1060 0.7989 0.049 Uiso 1 1 calc R
C16 C 0.4613(3) 0.11879(15) 0.92537(12) 0.0473(4) Uani 1 1 d .
H16A H 0.3121 0.1091 0.9362 0.057 Uiso 1 1 calc R
H16B H 0.5133 0.0563 0.9507 0.057 Uiso 1 1 calc R
C17 C 0.6152(3) 0.25853(15) 0.98757(12) 0.0413(4) Uani 1 1 d .
C18 C 0.8353(3) 0.31165(15) 1.04752(12) 0.0421(4) Uani 1 1 d .
C19 C 0.8898(3) 0.45202(17) 1.09318(12) 0.0450(4) Uani 1 1 d .
C20 C 1.0983(3) 0.5577(2) 1.16546(14) 0.0612(5) Uani 1 1 d .
H20A H 1.0900 0.6449 1.1710 0.092 Uiso 1 1 calc R
H20B H 1.2260 0.5484 1.1396 0.092 Uiso 1 1 calc R
H20C H 1.1141 0.5483 1.2326 0.092 Uiso 1 1 calc R
O1 O 1.1615(3) 0.29569(18) 1.12247(14) 0.0985(6) Uani 1 1 d .
O2 O 0.9220(3) 0.12050(17) 1.00114(16) 0.1033(6) 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 0.0033 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
C1 N1 C15 117.61(12)
C1 N1 C7 114.60(13)
C15 N1 C7 111.73(12)
O1 N2 O2 122.82(16)
O1 N2 C18 118.53(17)
O2 N2 C18 118.59(17)
C19 N3 N4 105.45(13)
C17 N4 N3 114.06(14)
C2 C1 C6 117.95(15)
C2 C1 N1 123.77(14)
C6 C1 N1 118.22(14)
C3 C2 C1 120.57(16)
C4 C3 C2 120.78(18)
C5 C4 C3 118.95(18)
C4 C5 C6 120.98(18)
C5 C6 C1 120.73(17)
N1 C7 C8 111.59(13)
C9 C8 C7 111.65(15)
C14 C9 C10 118.37(16)
C14 C9 C8 120.30(15)
C10 C9 C8 121.33(16)
C11 C10 C9 121.74(18)
C10 C11 C12 120.05(17)
C11 C12 C13 119.49(17)
C12 C13 C14 120.94(17)
C9 C14 C13 119.39(15)
C9 C14 C15 121.35(14)
C13 C14 C15 119.22(14)
N1 C15 C14 114.57(13)
N1 C15 C16 109.25(12)
C14 C15 C16 109.92(13)
C17 C16 C15 114.12(13)
N4 C17 C18 103.88(14)
N4 C17 C16 122.79(15)
C18 C17 C16 133.27(14)
C17 C18 C19 107.89(13)
C17 C18 N2 125.83(15)
C19 C18 N2 126.26(16)
N3 C19 C18 108.70(14)
N3 C19 C20 120.19(16)
C18 C19 C20 131.11(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.4224(19)
N1 C15 1.4645(19)
N1 C7 1.474(2)
N2 O1 1.219(2)
N2 O2 1.229(2)
N2 C18 1.413(2)
N3 C19 1.321(2)
N3 N4 1.3673(19)
N4 C17 1.3285(19)
C1 C2 1.389(2)
C1 C6 1.397(2)
C2 C3 1.384(2)
C3 C4 1.378(3)
C4 C5 1.374(3)
C5 C6 1.374(3)
C7 C8 1.515(3)
C8 C9 1.513(2)
C9 C14 1.391(2)
C9 C10 1.396(2)
C10 C11 1.368(3)
C11 C12 1.376(3)
C12 C13 1.380(2)
C13 C14 1.399(2)
C14 C15 1.520(2)
C15 C16 1.545(2)
C16 C17 1.490(2)
C17 C18 1.386(2)
C18 C19 1.411(2)
C19 C20 1.483(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203112
