#------------------------------------------------------------------------------
#$Date: 2019-11-28 21:25:23 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244665 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/93/7239353.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_7239353
loop_
_publ_author_name
'Das, Deb K.'
'Sarkar, Satavisha'
'Khan, Abu T.'
'Saravanan, Parameswaran'
'Patra, Sanjukta'
_publ_section_title
;
 Synthesis of fused tetrahydropyrido[2,3-c]coumarin derivatives as
 potential inhibitors for dopamine d3 receptors, catalyzed by hydrated
 ferric sulfate
;
_journal_issue                   7
_journal_name_full               'RSC Adv.'
_journal_page_first              3581
_journal_paper_doi               10.1039/C3RA45174G
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C18 H18 N O4'
_chemical_formula_weight         312.33
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.828(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8099(5)
_cell_length_b                   9.7399(5)
_cell_length_c                   12.7370(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1461.83(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.860
_diffrn_measured_fraction_theta_max 0.860
_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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22111
_diffrn_reflns_theta_full        34.04
_diffrn_reflns_theta_max         34.04
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.101
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         5141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0503
_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)+(0.0500P)²+0.2096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1292
_reflns_number_gt                3048
_reflns_number_total             5141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra45174g.txt
_cod_data_source_block           ac-cis
_cod_database_code               7239353
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.65738(7) 0.53700(9) 1.09775(7) 0.0494(2) Uani 1 1 d .
O2 O 0.80726(8) 0.59710(9) 1.01403(7) 0.0573(3) Uani 1 1 d .
O3 O 0.88719(8) 0.16445(11) 0.67610(7) 0.0625(3) Uani 1 1 d .
C12 C 0.84655(12) 0.06080(15) 0.95961(12) 0.0615(4) Uani 1 1 d .
H12A H 0.8958 -0.0032 0.9262 0.074 Uiso 1 1 calc R
H12B H 0.8925 0.1329 0.9933 0.074 Uiso 1 1 calc R
N1 N 0.81307(9) 0.36008(12) 0.90337(8) 0.0472(3) Uani 1 1 d .
C8 C 0.73016(9) 0.37858(11) 0.97303(8) 0.0390(2) Uani 1 1 d .
C7 C 0.65245(9) 0.28214(11) 0.99465(9) 0.0403(2) Uani 1 1 d .
C9 C 0.73609(10) 0.51114(12) 1.02740(9) 0.0430(3) Uani 1 1 d .
C6 C 0.56807(9) 0.31585(12) 1.06764(9) 0.0419(3) Uani 1 1 d .
C1 C 0.57254(10) 0.44378(13) 1.11673(9) 0.0432(3) Uani 1 1 d .
C13 C 0.75793(11) 0.12064(13) 0.87964(10) 0.0511(3) Uani 1 1 d .
H13 H 0.7389 0.0510 0.8258 0.061 Uiso 1 1 calc R
C10 C 0.65498(11) 0.14088(13) 0.94526(11) 0.0523(3) Uani 1 1 d .
H10 H 0.5851 0.1263 0.9007 0.063 Uiso 1 1 calc R
C15 C 0.90020(11) 0.23356(14) 0.76911(10) 0.0503(3) Uani 1 1 d .
C5 C 0.47804(11) 0.22969(14) 1.09097(12) 0.0558(3) Uani 1 1 d .
H5 H 0.4709 0.1441 1.0589 0.067 Uiso 1 1 calc R
C14 C 0.79411(10) 0.25169(14) 0.82505(9) 0.0479(3) Uani 1 1 d .
H14 H 0.7329 0.2801 0.7739 0.057 Uiso 1 1 calc R
O4 O 0.66425(10) 0.03801(10) 1.02542(10) 0.0760(3) Uani 1 1 d .
C2 C 0.49430(11) 0.48446(16) 1.18639(10) 0.0555(3) Uani 1 1 d .
H2 H 0.4997 0.5708 1.2175 0.067 Uiso 1 1 calc R
C4 C 0.40016(11) 0.26956(16) 1.16041(13) 0.0654(4) Uani 1 1 d .
H4 H 0.3412 0.2107 1.1747 0.078 Uiso 1 1 calc R
C3 C 0.40852(12) 0.39639(17) 1.20930(12) 0.0641(4) Uani 1 1 d .
H3 H 0.3564 0.4218 1.2573 0.077 Uiso 1 1 calc R
C18 C 0.99188(13) 0.15710(17) 0.63741(12) 0.0657(4) Uani 1 1 d .
H18 H 1.0073 0.1154 0.5743 0.079 Uiso 1 1 calc R
C17 C 1.06787(13) 0.21723(18) 0.70196(14) 0.0700(4) Uani 1 1 d .
H17 H 1.1451 0.2255 0.6930 0.084 Uiso 1 1 calc R
C16 C 1.00874(12) 0.26755(19) 0.78877(13) 0.0743(5) Uani 1 1 d .
H16 H 1.0400 0.3146 0.8473 0.089 Uiso 1 1 calc R
C11 C 0.77738(15) -0.0115(2) 1.03800(15) 0.0802(5) Uani 1 1 d .
H11A H 0.7787 -0.1098 1.0261 0.096 Uiso 1 1 calc R
H11B H 0.8088 0.0066 1.1090 0.096 Uiso 1 1 calc R
H1N H 0.8420(12) 0.4353(16) 0.8806(11) 0.061(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
C9 O1 C1 121.93(9)
C15 O3 C18 106.74(11)
C11 C12 C13 104.04(12)
C8 N1 C14 116.87(10)
C7 C8 N1 124.14(11)
C7 C8 C9 121.80(10)
N1 C8 C9 113.99(10)
C8 C7 C6 118.62(10)
C8 C7 C10 120.89(11)
C6 C7 C10 120.48(10)
O2 C9 O1 118.60(11)
O2 C9 C8 123.84(11)
O1 C9 C8 117.55(10)
C1 C6 C5 116.54(11)
C1 C6 C7 118.99(10)
C5 C6 C7 124.45(11)
C2 C1 O1 116.53(11)
C2 C1 C6 122.54(12)
O1 C1 C6 120.93(10)
C12 C13 C14 114.99(11)
C12 C13 C10 102.63(11)
C14 C13 C10 113.37(10)
O4 C10 C7 110.05(11)
O4 C10 C13 105.87(10)
C7 C10 C13 112.44(10)
C16 C15 O3 109.74(12)
C16 C15 C14 135.16(12)
O3 C15 C14 115.09(11)
C4 C5 C6 121.13(14)
N1 C14 C15 108.45(10)
N1 C14 C13 109.15(10)
C15 C14 C13 112.80(11)
C11 O4 C10 110.19(11)
C3 C2 C1 119.46(14)
C5 C4 C3 120.75(13)
C2 C3 C4 119.56(13)
C17 C18 O3 110.40(13)
C18 C17 C16 106.72(13)
C15 C16 C17 106.41(14)
O4 C11 C12 108.35(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.3571(14)
O1 C1 1.3853(14)
O2 C9 1.2064(14)
O3 C15 1.3622(15)
O3 C18 1.3631(17)
C12 C11 1.506(2)
C12 C13 1.527(2)
N1 C8 1.3764(15)
N1 C14 1.4595(15)
C8 C7 1.3543(16)
C8 C9 1.4646(16)
C7 C6 1.4453(16)
C7 C10 1.5140(17)
C6 C1 1.3935(17)
C6 C5 1.4019(17)
C1 C2 1.3811(17)
C13 C14 1.5281(19)
C13 C10 1.5334(18)
C10 O4 1.4296(17)
C15 C16 1.3313(19)
C15 C14 1.4926(17)
C5 C4 1.3739(19)
O4 C11 1.419(2)
C2 C3 1.374(2)
C4 C3 1.384(2)
C18 C17 1.314(2)
C17 C16 1.433(2)
