#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:43:49 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240251.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_7240251
loop_
_publ_author_name
'Palanimuthu, Arunan'
'Chen, Chinpiao'
'Lee, Gene-Hsian'
_publ_section_title
;
 Synthesis of highly substituted tetrahydroquinolines using ethyl
 cyanoacetate via aza-Michael--Michael addition
;
_journal_issue                   23
_journal_name_full               'RSC Advances'
_journal_page_first              13591
_journal_page_last               13600
_journal_paper_doi               10.1039/D0RA01264E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C25 H27 N3 O6'
_chemical_formula_weight         465.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-03 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.5727(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8148(3)
_cell_length_b                   9.6634(2)
_cell_length_c                   20.8234(5)
_cell_measurement_reflns_used    7578
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.03
_cell_measurement_theta_min      3.78
_cell_volume                     2350.87(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11420
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.990
_diffrn_reflns_theta_min         4.294
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4394
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0392
_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)+(0.0421P)²+0.8741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3715
_reflns_number_total             4394
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra01264e3.cif
_cod_data_source_block           ic18499
_cod_depositor_comments
'Adding full bibliography for 7240251--7240252.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240251
_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. 
;
_shelx_estimated_absorpt_t_min   0.885
_shelx_estimated_absorpt_t_max   0.968
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.90794(11) 0.32296(16) 0.18259(8) 0.0605(4) Uani 1 1 d . . . . .
O2 O 1.01279(10) 0.47810(15) 0.23607(7) 0.0548(3) Uani 1 1 d . . . . .
O3 O 0.38437(11) 1.29265(13) 0.13625(5) 0.0447(3) Uani 1 1 d . . . . .
O4 O 0.28129(8) 1.25132(11) 0.03742(5) 0.0327(2) Uani 1 1 d . . . . .
O5 O 0.65644(10) 1.05387(14) 0.19150(6) 0.0455(3) Uani 1 1 d . . . . .
O6 O 0.69557(9) 0.95053(14) 0.10131(6) 0.0429(3) Uani 1 1 d D . . . .
N1 N 0.42102(10) 0.71878(16) 0.19791(7) 0.0375(3) Uani 1 1 d . . . . .
H1 H 0.4161(16) 0.659(2) 0.2286(10) 0.046(5) Uiso 1 1 d . . . . .
N2 N 0.49303(12) 0.73913(16) 0.03439(6) 0.0401(3) Uani 1 1 d . . . . .
N3 N 0.92035(11) 0.43497(16) 0.20979(7) 0.0405(3) Uani 1 1 d . . . . .
C1 C 0.31733(12) 0.78203(17) 0.17476(6) 0.0307(3) Uani 1 1 d . . . . .
C2 C 0.21536(13) 0.71256(18) 0.18087(7) 0.0363(3) Uani 1 1 d . . . . .
H2A H 0.2183 0.6267 0.2033 0.044 Uiso 1 1 calc R U . . .
C3 C 0.11119(13) 0.7671(2) 0.15483(8) 0.0426(4) Uani 1 1 d . . . . .
H3 H 0.0427 0.7194 0.1596 0.051 Uiso 1 1 calc R U . . .
C4 C 0.10607(13) 0.8911(2) 0.12182(10) 0.0506(5) Uani 1 1 d . . . . .
H4 H 0.0342 0.9281 0.1030 0.061 Uiso 1 1 calc R U . . .
C5 C 0.20599(13) 0.9613(2) 0.11620(8) 0.0417(4) Uani 1 1 d . . . . .
H5 H 0.2017 1.0471 0.0937 0.050 Uiso 1 1 calc R U . . .
C6 C 0.31271(11) 0.90951(17) 0.14265(6) 0.0293(3) Uani 1 1 d . . . . .
C7 C 0.42195(11) 0.98875(16) 0.13865(6) 0.0274(3) Uani 1 1 d . . . . .
H7 H 0.4372 1.0485 0.1782 0.033 Uiso 1 1 calc R U . . .
C8 C 0.52395(11) 0.88657(16) 0.14097(6) 0.0264(3) Uani 1 1 d . . . . .
C9 C 0.52886(11) 0.79187(16) 0.20228(6) 0.0301(3) Uani 1 1 d . . . . .
H9 H 0.5384 0.8516 0.2420 0.036 Uiso 1 1 calc R U . . .
C10 C 0.62927(12) 0.69160(17) 0.20704(6) 0.0303(3) Uani 1 1 d . . . . .
C11 C 0.61775(12) 0.55968(18) 0.18050(7) 0.0354(3) Uani 1 1 d . . . . .
H11 H 0.5446 0.5279 0.1609 0.042 Uiso 1 1 calc R U . . .
C12 C 0.71258(13) 0.47376(18) 0.18237(8) 0.0371(3) Uani 1 1 d . . . . .
H12 H 0.7049 0.3830 0.1647 0.045 Uiso 1 1 calc R U . . .
C13 C 0.81837(12) 0.52300(17) 0.21047(7) 0.0332(3) Uani 1 1 d . . . . .
C14 C 0.83244(12) 0.65188(17) 0.23852(7) 0.0347(3) Uani 1 1 d . . . . .
H14 H 0.9057 0.6827 0.2584 0.042 Uiso 1 1 calc R U . . .
C15 C 0.73693(12) 0.73549(17) 0.23696(7) 0.0337(3) Uani 1 1 d . . . . .
H15 H 0.7448 0.8244 0.2566 0.040 Uiso 1 1 calc R U . . .
C16 C 0.41578(12) 1.08420(16) 0.07925(7) 0.0307(3) Uani 1 1 d . . . . .
H16A H 0.4943 1.1010 0.0698 0.037 Uiso 1 1 calc R U . . .
H16B H 0.3724 1.0369 0.0411 0.037 Uiso 1 1 calc R U . . .
C17 C 0.35952(12) 1.22181(16) 0.08875(7) 0.0313(3) Uani 1 1 d . . . . .
C18 C 0.21806(13) 1.38411(18) 0.03196(8) 0.0397(4) Uani 1 1 d . . . . .
C19 C 0.15078(19) 1.3728(2) -0.03583(10) 0.0646(6) Uani 1 1 d . . . . .
H19A H 0.2035 1.3551 -0.0671 0.097 Uiso 1 1 calc R U . . .
H19B H 0.1096 1.4596 -0.0471 0.097 Uiso 1 1 calc R U . . .
H19C H 0.0958 1.2966 -0.0372 0.097 Uiso 1 1 calc R U . . .
C20 C 0.30052(18) 1.5043(2) 0.03628(11) 0.0581(5) Uani 1 1 d . . . . .
H20A H 0.3418 1.5110 0.0806 0.087 Uiso 1 1 calc R U . . .
H20B H 0.2580 1.5901 0.0251 0.087 Uiso 1 1 calc R U . . .
H20C H 0.3553 1.4897 0.0059 0.087 Uiso 1 1 calc R U . . .
C21 C 0.13996(17) 1.3883(2) 0.08370(11) 0.0589(5) Uani 1 1 d . . . . .
H21A H 0.0902 1.3067 0.0794 0.088 Uiso 1 1 calc R U . . .
H21B H 0.0929 1.4722 0.0782 0.088 Uiso 1 1 calc R U . . .
H21C H 0.1864 1.3889 0.1268 0.088 Uiso 1 1 calc R U . . .
C22 C 0.50928(11) 0.80186(16) 0.08122(7) 0.0281(3) Uani 1 1 d . . . . .
C23 C 0.63367(11) 0.97307(16) 0.14773(7) 0.0307(3) Uani 1 1 d . . . . .
C24 C 0.8045(5) 1.0212(7) 0.0979(3) 0.0562(13) Uani 0.577(4) 1 d D U P A 1
H24A H 0.8541 0.9621 0.0750 0.067 Uiso 0.577(4) 1 calc R U P A 1
H24B H 0.8448 1.0396 0.1422 0.067 Uiso 0.577(4) 1 calc R U P A 1
C25 C 0.7800(3) 1.1555(5) 0.06182(18) 0.0572(8) Uani 0.577(4) 1 d D U P A 1
H25A H 0.8514 1.2074 0.0624 0.086 Uiso 0.577(4) 1 calc R U P A 1
H25B H 0.7261 1.2104 0.0828 0.086 Uiso 0.577(4) 1 calc R U P A 1
H25C H 0.7465 1.1362 0.0168 0.086 Uiso 0.577(4) 1 calc R U P A 1
C24' C 0.7978(8) 1.0401(11) 0.1150(4) 0.0562(13) Uani 0.423(4) 1 d D . P A 2
H24C H 0.8618 0.9885 0.1403 0.067 Uiso 0.423(4) 1 calc R U P A 2
H24D H 0.7807 1.1219 0.1405 0.067 Uiso 0.423(4) 1 calc R U P A 2
C25' C 0.8292(5) 1.0842(7) 0.0515(2) 0.0572(8) Uani 0.423(4) 1 d D . P A 2
H25D H 0.9020 1.1346 0.0588 0.086 Uiso 0.423(4) 1 calc R U P A 2
H25E H 0.7692 1.1447 0.0292 0.086 Uiso 0.423(4) 1 calc R U P A 2
H25F H 0.8370 1.0025 0.0246 0.086 Uiso 0.423(4) 1 calc R U P A 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O4 C18 121.84(12) . . ?
C23 O6 C24 123.1(3) . . ?
C23 O6 C24' 106.8(3) . . ?
C1 N1 C9 121.96(13) . . ?
O2 N3 O1 123.29(14) . . ?
O2 N3 C13 118.44(15) . . ?
O1 N3 C13 118.27(14) . . ?
N1 C1 C6 121.52(13) . . ?
N1 C1 C2 118.90(14) . . ?
C6 C1 C2 119.50(13) . . ?
C3 C2 C1 120.79(16) . . ?
C2 C3 C4 120.05(15) . . ?
C3 C4 C5 119.64(15) . . ?
C4 C5 C6 121.67(16) . . ?
C5 C6 C1 118.32(14) . . ?
C5 C6 C7 121.73(14) . . ?
C1 C6 C7 119.93(12) . . ?
C6 C7 C16 114.18(11) . . ?
C6 C7 C8 109.92(12) . . ?
C16 C7 C8 110.50(11) . . ?
C22 C8 C23 111.79(11) . . ?
C22 C8 C7 109.44(11) . . ?
C23 C8 C7 107.34(12) . . ?
C22 C8 C9 110.39(12) . . ?
C23 C8 C9 108.44(11) . . ?
C7 C8 C9 109.35(10) . . ?
N1 C9 C10 111.30(13) . . ?
N1 C9 C8 107.99(11) . . ?
C10 C9 C8 111.02(11) . . ?
C11 C10 C15 119.04(14) . . ?
C11 C10 C9 121.94(13) . . ?
C15 C10 C9 118.98(14) . . ?
C10 C11 C12 120.43(14) . . ?
C13 C12 C11 118.69(15) . . ?
C14 C13 C12 122.39(14) . . ?
C14 C13 N3 118.60(13) . . ?
C12 C13 N3 119.01(15) . . ?
C13 C14 C15 118.18(14) . . ?
C14 C15 C10 121.22(15) . . ?
C17 C16 C7 113.06(11) . . ?
O3 C17 O4 126.27(15) . . ?
O3 C17 C16 123.35(13) . . ?
O4 C17 C16 110.38(12) . . ?
O4 C18 C20 110.38(13) . . ?
O4 C18 C19 101.39(14) . . ?
C20 C18 C19 110.77(17) . . ?
O4 C18 C21 108.76(14) . . ?
C20 C18 C21 113.05(17) . . ?
C19 C18 C21 111.85(16) . . ?
N2 C22 C8 176.82(15) . . ?
O5 C23 O6 125.46(14) . . ?
O5 C23 C8 121.07(13) . . ?
O6 C23 C8 113.46(12) . . ?
O6 C24 C25 108.7(5) . . ?
O6 C24' C25' 107.5(6) . . ?
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 N3 1.220(2) . ?
O2 N3 1.2197(19) . ?
O3 C17 1.2028(19) . ?
O4 C17 1.3355(17) . ?
O4 C18 1.4807(19) . ?
O5 C23 1.1998(19) . ?
O6 C23 1.3144(18) . ?
O6 C24 1.468(6) . ?
O6 C24' 1.478(8) . ?
N1 C1 1.3894(19) . ?
N1 C9 1.4477(19) . ?
N2 C22 1.140(2) . ?
N3 C13 1.4767(19) . ?
C1 C6 1.399(2) . ?
C1 C2 1.401(2) . ?
C2 C3 1.374(2) . ?
C3 C4 1.378(3) . ?
C4 C5 1.382(2) . ?
C5 C6 1.392(2) . ?
C6 C7 1.5136(19) . ?
C7 C16 1.5360(19) . ?
C7 C8 1.5532(18) . ?
C8 C22 1.4779(19) . ?
C8 C23 1.5313(19) . ?
C8 C9 1.5648(19) . ?
C9 C10 1.5235(19) . ?
C10 C11 1.388(2) . ?
C10 C15 1.396(2) . ?
C11 C12 1.390(2) . ?
C12 C13 1.383(2) . ?
C13 C14 1.375(2) . ?
C14 C15 1.384(2) . ?
C16 C17 1.513(2) . ?
C18 C20 1.510(3) . ?
C18 C19 1.517(2) . ?
C18 C21 1.520(3) . ?
C24 C25 1.506(7) . ?
C24' C25' 1.488(7) . ?
