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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/98/7219861.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_7219861
loop_
_publ_author_name
'Basireddy, Venkata Subba Reddy'
'Ramisetti, Anjibabu'
'Reddy, Jagan Mohan'
'Balasubramanian, Sridhar'
'Ramalingamurthy, T.'
'Pranathi, Patlollu'
'kalivendi, shasi v'
'Prabhakar Rao, Tadikamalla'
_publ_section_title
;
 A short and highly convergent approach for the synthesis of rutaecarpine
 derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA14093A
_journal_year                    2015
_chemical_formula_moiety         'C19 H17 N3 O'
_chemical_formula_sum            'C19 H17 N3 O'
_chemical_formula_weight         303.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-09-11 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.007(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2058(10)
_cell_length_b                   5.2630(4)
_cell_length_c                   22.7073(17)
_cell_measurement_reflns_used    4684
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.90
_cell_volume                     1554.2(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14139
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0556P)²+0.4988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                2431
_reflns_number_total             2745
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4ra14093a2.cif
_cod_data_source_block           aw58m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7219861
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.66619(13) 0.6520(4) 0.85684(8) 0.0463(4) Uani 1 1 d .
C2 C 0.65422(16) 0.7012(4) 0.79565(8) 0.0579(5) Uani 1 1 d .
H2 H 0.6890 0.6061 0.7710 0.070 Uiso 1 1 calc R
C3 C 0.58934(16) 0.8950(5) 0.77314(9) 0.0664(6) Uani 1 1 d .
H3 H 0.5800 0.9310 0.7325 0.080 Uiso 1 1 calc R
C4 C 0.53685(16) 1.0397(5) 0.80999(9) 0.0658(6) Uani 1 1 d .
H4 H 0.4936 1.1704 0.7935 0.079 Uiso 1 1 calc R
C5 C 0.54838(14) 0.9912(4) 0.87012(9) 0.0549(5) Uani 1 1 d .
H5 H 0.5137 1.0890 0.8943 0.066 Uiso 1 1 calc R
C6 C 0.61267(13) 0.7938(4) 0.89465(8) 0.0443(4) Uani 1 1 d .
C7 C 0.64330(13) 0.6938(3) 0.95352(8) 0.0417(4) Uani 1 1 d .
C8 C 0.71189(12) 0.5053(3) 0.94934(7) 0.0404(4) Uani 1 1 d .
C9 C 0.76505(12) 0.3500(3) 1.00005(7) 0.0410(4) Uani 1 1 d .
H9 H 0.7570 0.1706 0.9886 0.049 Uiso 1 1 calc R
C10 C 0.93251(14) 0.3088(4) 1.06225(9) 0.0583(5) Uani 1 1 d .
C11 C 0.87386(14) 0.2022(4) 1.10644(8) 0.0511(5) Uani 1 1 d .
C12 C 0.92317(16) 0.0615(5) 1.15494(10) 0.0655(6) Uani 1 1 d .
H12 H 0.9919 0.0172 1.1572 0.079 Uiso 1 1 calc R
C13 C 0.87111(18) -0.0125(4) 1.19953(10) 0.0663(6) Uani 1 1 d .
H13 H 0.9038 -0.1114 1.2312 0.080 Uiso 1 1 calc R
C14 C 0.77029(18) 0.0607(4) 1.19711(9) 0.0598(5) Uani 1 1 d .
H14 H 0.7359 0.0157 1.2280 0.072 Uiso 1 1 calc R
C15 C 0.71998(15) 0.1992(4) 1.14967(8) 0.0518(5) Uani 1 1 d .
H15 H 0.6522 0.2492 1.1488 0.062 Uiso 1 1 calc R
C16 C 0.77015(14) 0.2650(3) 1.10286(8) 0.0441(4) Uani 1 1 d .
C17 C 0.68970(15) 0.6551(4) 1.06243(8) 0.0526(5) Uani 1 1 d .
H17A H 0.7516 0.7575 1.0670 0.063 Uiso 1 1 calc R
H17B H 0.6625 0.6656 1.0994 0.063 Uiso 1 1 calc R
C18 C 0.61150(13) 0.7607(3) 1.01180(8) 0.0448(4) Uani 1 1 d .
H18A H 0.5442 0.6896 1.0133 0.054 Uiso 1 1 calc R
H18B H 0.6073 0.9438 1.0156 0.054 Uiso 1 1 calc R
C19 C 0.79233(15) 0.2901(4) 0.86908(9) 0.0572(5) Uani 1 1 d .
H19A H 0.7580 0.2237 0.8315 0.086 Uiso 1 1 calc R
H19B H 0.8069 0.1539 0.8974 0.086 Uiso 1 1 calc R
H19C H 0.8555 0.3698 0.8638 0.086 Uiso 1 1 calc R
N1 N 0.72663(11) 0.4756(3) 0.89109(6) 0.0460(4) Uani 1 1 d .
N2 N 0.87500(11) 0.4072(3) 1.01319(7) 0.0534(4) Uani 1 1 d .
N3 N 0.71561(11) 0.3902(3) 1.05177(6) 0.0431(4) Uani 1 1 d .
O1 O 1.02765(10) 0.3190(4) 1.07207(8) 0.0872(6) Uani 1 1 d .
H1N H 0.9018(17) 0.487(4) 0.9846(10) 0.065(6) 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
N1 C1 C2 130.03(17)
N1 C1 C6 108.36(15)
C2 C1 C6 121.60(18)
C3 C2 C1 117.66(19)
C3 C2 H2 121.2
C1 C2 H2 121.2
C2 C3 C4 121.55(19)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 120.8(2)
C5 C4 H4 119.6
C3 C4 H4 119.6
C4 C5 C6 119.40(19)
C4 C5 H5 120.3
C6 C5 H5 120.3
C5 C6 C1 118.93(17)
C5 C6 C7 134.58(17)
C1 C6 C7 106.46(16)
C8 C7 C6 106.72(15)
C8 C7 C18 121.75(16)
C6 C7 C18 131.53(16)
C7 C8 N1 110.92(16)
C7 C8 C9 125.39(15)
N1 C8 C9 123.69(15)
N3 C9 N2 111.99(14)
N3 C9 C8 109.13(14)
N2 C9 C8 111.32(14)
N3 C9 H9 108.1
N2 C9 H9 108.1
C8 C9 H9 108.1
O1 C10 N2 122.96(18)
O1 C10 C11 121.90(18)
N2 C10 C11 115.00(16)
C12 C11 C16 119.41(18)
C12 C11 C10 120.67(18)
C16 C11 C10 119.60(17)
C13 C12 C11 120.6(2)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C14 119.6(2)
C12 C13 H13 120.2
C14 C13 H13 120.2
C15 C14 C13 120.82(18)
C15 C14 H14 119.6
C13 C14 H14 119.6
C14 C15 C16 120.14(19)
C14 C15 H15 119.9
C16 C15 H15 119.9
C15 C16 C11 119.27(18)
C15 C16 N3 119.98(17)
C11 C16 N3 120.74(15)
N3 C17 C18 111.86(15)
N3 C17 H17A 109.2
C18 C17 H17A 109.2
N3 C17 H17B 109.2
C18 C17 H17B 109.2
H17A C17 H17B 107.9
C7 C18 C17 109.03(15)
C7 C18 H18A 109.9
C17 C18 H18A 109.9
C7 C18 H18B 109.9
C17 C18 H18B 109.9
H18A C18 H18B 108.3
N1 C19 H19A 109.5
N1 C19 H19B 109.5
H19A C19 H19B 109.5
N1 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C1 N1 C8 107.54(14)
C1 N1 C19 125.65(15)
C8 N1 C19 126.81(16)
C10 N2 C9 119.33(15)
C10 N2 H1N 123.0(14)
C9 N2 H1N 116.9(14)
C16 N3 C9 110.95(14)
C16 N3 C17 114.01(14)
C9 N3 C17 114.98(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.374(2)
C1 C2 1.395(3)
C1 C6 1.416(3)
C2 C3 1.372(3)
C2 H2 0.9300
C3 C4 1.401(3)
C3 H3 0.9300
C4 C5 1.371(3)
C4 H4 0.9300
C5 C6 1.395(3)
C5 H5 0.9300
C6 C7 1.428(2)
C7 C8 1.358(2)
C7 C18 1.498(2)
C8 N1 1.379(2)
C8 C9 1.485(2)
C9 N3 1.455(2)
C9 N2 1.462(2)
C9 H9 0.9800
C10 O1 1.238(2)
C10 N2 1.339(3)
C10 C11 1.480(3)
C11 C12 1.391(3)
C11 C16 1.397(3)
C12 C13 1.375(3)
C12 H12 0.9300
C13 C14 1.378(3)
C13 H13 0.9300
C14 C15 1.373(3)
C14 H14 0.9300
C15 C16 1.391(2)
C15 H15 0.9300
C16 N3 1.417(2)
C17 N3 1.465(2)
C17 C18 1.511(3)
C17 H17A 0.9700
C17 H17B 0.9700
C18 H18A 0.9700
C18 H18B 0.9700
C19 N1 1.452(2)
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
N2 H1N 0.90(2)
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
N2 H1N O1 0.90(2) 2.00(2) 2.888(2) 174(2) 3_767
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
N1 C1 C2 C3 -178.67(19)
C6 C1 C2 C3 0.8(3)
C1 C2 C3 C4 0.2(3)
C2 C3 C4 C5 -0.3(3)
C3 C4 C5 C6 -0.5(3)
C4 C5 C6 C1 1.4(3)
C4 C5 C6 C7 179.0(2)
N1 C1 C6 C5 178.01(16)
C2 C1 C6 C5 -1.5(3)
N1 C1 C6 C7 -0.26(19)
C2 C1 C6 C7 -179.81(16)
C5 C6 C7 C8 -177.3(2)
C1 C6 C7 C8 0.55(19)
C5 C6 C7 C18 3.7(3)
C1 C6 C7 C18 -178.42(17)
C6 C7 C8 N1 -0.65(19)
C18 C7 C8 N1 178.44(15)
C6 C7 C8 C9 179.21(15)
C18 C7 C8 C9 -1.7(3)
C7 C8 C9 N3 12.8(2)
N1 C8 C9 N3 -167.34(14)
C7 C8 C9 N2 -111.29(19)
N1 C8 C9 N2 68.6(2)
O1 C10 C11 C12 -13.7(4)
N2 C10 C11 C12 170.5(2)
O1 C10 C11 C16 159.7(2)
N2 C10 C11 C16 -16.1(3)
C16 C11 C12 C13 -0.9(3)
C10 C11 C12 C13 172.5(2)
C11 C12 C13 C14 -2.2(4)
C12 C13 C14 C15 2.3(3)
C13 C14 C15 C16 0.8(3)
C14 C15 C16 C11 -3.9(3)
C14 C15 C16 N3 174.94(17)
C12 C11 C16 C15 3.9(3)
C10 C11 C16 C15 -169.56(18)
C12 C11 C16 N3 -174.89(18)
C10 C11 C16 N3 11.6(3)
C8 C7 C18 C17 18.3(2)
C6 C7 C18 C17 -162.83(17)
N3 C17 C18 C7 -46.8(2)
C2 C1 N1 C8 179.37(19)
C6 C1 N1 C8 -0.12(19)
C2 C1 N1 C19 -1.6(3)
C6 C1 N1 C19 178.93(16)
C7 C8 N1 C1 0.49(19)
C9 C8 N1 C1 -179.37(15)
C7 C8 N1 C19 -178.54(16)
C9 C8 N1 C19 1.6(3)
O1 C10 N2 C9 169.7(2)
C11 C10 N2 C9 -14.5(3)
N3 C9 N2 C10 49.1(2)
C8 C9 N2 C10 171.56(18)
C15 C16 N3 C9 -156.59(16)
C11 C16 N3 C9 22.2(2)
C15 C16 N3 C17 71.7(2)
C11 C16 N3 C17 -109.50(19)
N2 C9 N3 C16 -50.52(19)
C8 C9 N3 C16 -174.23(14)
N2 C9 N3 C17 80.71(19)
C8 C9 N3 C17 -43.00(19)
C18 C17 N3 C16 -166.68(14)
C18 C17 N3 C9 63.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139200017
