#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:35:33 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225114 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/70/7157077.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_7157077
loop_
_publ_author_name
'Gupta, Vijay'
'Sahu, Debashish'
'Jain, Shailja'
'Vanka, Kumar'
'Singh, Ravi P.'
_publ_section_title
;
 Diastereoselective multi-component tandem condensation: synthesis of
 2-amino-4-(2-furanone)-4H-chromene-3-carbonitriles.
;
_journal_issue                   39
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8853
_journal_page_last               8857
_journal_paper_doi               10.1039/c9ob01345h
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C14 H10 N2 O3'
_chemical_formula_sum            'C14 H10 N2 O3'
_chemical_formula_weight         254.24
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-01-07 deposited with the CCDC.    2019-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.075(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3319(9)
_cell_length_b                   6.1459(4)
_cell_length_c                   13.6122(8)
_cell_measurement_reflns_used    7075
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.320
_cell_measurement_theta_min      2.29
_cell_volume                     1232.50(13)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.17
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23169
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.320
_diffrn_reflns_theta_min         3.038
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528.0
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0565
_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)+(0.1000P)²+0.6905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1677
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2418
_reflns_number_total             3064
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ob01345h2.cif
_cod_data_source_block           vj2_0ma_a_a
_cod_depositor_comments
'Adding full bibliography for 7157076--7157078.cif.'
_cod_database_code               7157077
_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.
;
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
O1 O 0.69026(8) 0.44140(18) 0.17743(9) 0.0177(3) Uani 1 1 d . .
O2 O 0.71543(8) 0.33786(19) 0.42350(9) 0.0168(3) Uani 1 1 d . .
O3 O 0.75016(10) 0.6547(2) 0.50501(10) 0.0267(3) Uani 1 1 d . .
N1 N 0.82332(10) 0.6008(2) 0.19528(11) 0.0182(3) Uani 1 1 d . .
H1A H 0.7917 0.7060 0.1581 0.022 Uiso 1 1 calc R U
H1B H 0.8828 0.6107 0.2174 0.022 Uiso 1 1 calc R U
N2 N 0.99346(11) 0.2153(3) 0.32759(14) 0.0291(4) Uani 1 1 d . .
C8 C 0.81973(11) 0.2494(3) 0.27547(12) 0.0160(3) Uani 1 1 d . .
C7 C 0.76385(11) 0.0825(3) 0.31191(12) 0.0154(3) Uani 1 1 d . .
H7 H 0.7921 -0.0639 0.3108 0.018 Uiso 1 1 calc R U
C9 C 0.78091(11) 0.4252(3) 0.21828(12) 0.0150(3) Uani 1 1 d . .
C6 C 0.66936(11) 0.0792(3) 0.23969(12) 0.0157(3) Uani 1 1 d . .
C11 C 0.75885(11) 0.1291(3) 0.42200(12) 0.0162(3) Uani 1 1 d . .
H11 H 0.7230 0.0124 0.4442 0.019 Uiso 1 1 calc R U
C12 C 0.84896(12) 0.1535(3) 0.49904(12) 0.0192(4) Uani 1 1 d . .
H12 H 0.8938 0.0429 0.5173 0.023 Uiso 1 1 calc R U
C10 C 0.91544(12) 0.2329(3) 0.30477(13) 0.0192(4) Uani 1 1 d . .
C1 C 0.63718(11) 0.2573(3) 0.17789(12) 0.0164(3) Uani 1 1 d . .
C2 C 0.54951(12) 0.2668(3) 0.11354(13) 0.0208(4) Uani 1 1 d . .
H2 H 0.5293 0.3915 0.0722 0.025 Uiso 1 1 calc R U
C5 C 0.61035(12) -0.0957(3) 0.23487(14) 0.0207(4) Uani 1 1 d . .
H5 H 0.6308 -0.2207 0.2758 0.025 Uiso 1 1 calc R U
C14 C 0.77246(12) 0.4707(3) 0.49116(12) 0.0183(4) Uani 1 1 d . .
C13 C 0.85706(12) 0.3528(3) 0.53820(13) 0.0203(4) Uani 1 1 d . .
H13 H 0.9085 0.4092 0.5878 0.024 Uiso 1 1 calc R U
C4 C 0.52198(12) -0.0900(3) 0.17096(14) 0.0231(4) Uani 1 1 d . .
H4 H 0.4824 -0.2099 0.1688 0.028 Uiso 1 1 calc R U
C3 C 0.49200(12) 0.0915(3) 0.11053(14) 0.0236(4) Uani 1 1 d . .
H3 H 0.4318 0.0956 0.0669 0.028 Uiso 1 1 calc R U
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 118.27(12)
C14 O2 C11 109.32(12)
C9 N1 H1A 120.0
C9 N1 H1B 120.0
H1A N1 H1B 120.0
C9 C8 C10 118.13(15)
C9 C8 C7 121.87(14)
C10 C8 C7 119.92(14)
C8 C7 C6 108.99(13)
C8 C7 C11 112.18(13)
C6 C7 C11 109.70(13)
C8 C7 H7 108.6
C6 C7 H7 108.6
C11 C7 H7 108.6
N1 C9 O1 110.79(13)
N1 C9 C8 127.29(15)
O1 C9 C8 121.92(14)
C1 C6 C5 117.58(15)
C1 C6 C7 120.10(14)
C5 C6 C7 122.27(15)
O2 C11 C12 103.95(13)
O2 C11 C7 108.90(12)
C12 C11 C7 114.47(14)
O2 C11 H11 109.8
C12 C11 H11 109.8
C7 C11 H11 109.8
C13 C12 C11 109.88(15)
C13 C12 H12 125.1
C11 C12 H12 125.1
N2 C10 C8 178.6(2)
C6 C1 C2 122.46(16)
C6 C1 O1 122.24(14)
C2 C1 O1 115.29(14)
C3 C2 C1 118.87(17)
C3 C2 H2 120.6
C1 C2 H2 120.6
C4 C5 C6 121.05(17)
C4 C5 H5 119.5
C6 C5 H5 119.5
O3 C14 O2 120.79(15)
O3 C14 C13 130.23(16)
O2 C14 C13 108.98(14)
C12 C13 C14 107.86(15)
C12 C13 H13 126.1
C14 C13 H13 126.1
C3 C4 C5 119.74(17)
C3 C4 H4 120.1
C5 C4 H4 120.1
C2 C3 C4 120.29(16)
C2 C3 H3 119.9
C4 C3 H3 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.3502(19)
O1 C1 1.395(2)
O2 C14 1.354(2)
O2 C11 1.4479(19)
O3 C14 1.212(2)
N1 C9 1.341(2)
N1 H1A 0.8800
N1 H1B 0.8800
N2 C10 1.155(2)
C8 C9 1.368(2)
C8 C10 1.414(2)
C8 C7 1.506(2)
C7 C6 1.509(2)
C7 C11 1.548(2)
C7 H7 1.0000
C6 C1 1.385(2)
C6 C5 1.395(2)
C11 C12 1.493(2)
C11 H11 1.0000
C12 C13 1.328(3)
C12 H12 0.9500
C1 C2 1.388(2)
C2 C3 1.386(3)
C2 H2 0.9500
C5 C4 1.393(2)
C5 H5 0.9500
C14 C13 1.469(2)
C13 H13 0.9500
C4 C3 1.386(3)
C4 H4 0.9500
C3 H3 0.9500
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
C9 C8 C7 C6 26.2(2)
C10 C8 C7 C6 -157.07(15)
C9 C8 C7 C11 -95.47(18)
C10 C8 C7 C11 81.23(19)
C1 O1 C9 N1 168.58(14)
C1 O1 C9 C8 -12.0(2)
C10 C8 C9 N1 -8.2(3)
C7 C8 C9 N1 168.53(16)
C10 C8 C9 O1 172.40(15)
C7 C8 C9 O1 -10.8(2)
C8 C7 C6 C1 -21.3(2)
C11 C7 C6 C1 101.87(18)
C8 C7 C6 C5 161.13(16)
C11 C7 C6 C5 -75.68(19)
C14 O2 C11 C12 0.86(17)
C14 O2 C11 C7 -121.56(14)
C8 C7 C11 O2 61.68(16)
C6 C7 C11 O2 -59.61(16)
C8 C7 C11 C12 -54.15(18)
C6 C7 C11 C12 -175.44(13)
O2 C11 C12 C13 -1.23(19)
C7 C11 C12 C13 117.44(16)
C5 C6 C1 C2 0.6(3)
C7 C6 C1 C2 -177.03(16)
C5 C6 C1 O1 179.45(15)
C7 C6 C1 O1 1.8(2)
C9 O1 C1 C6 16.6(2)
C9 O1 C1 C2 -164.55(15)
C6 C1 C2 C3 -0.3(3)
O1 C1 C2 C3 -179.17(16)
C1 C6 C5 C4 -0.7(3)
C7 C6 C5 C4 176.91(16)
C11 O2 C14 O3 179.95(16)
C11 O2 C14 C13 -0.26(19)
C11 C12 C13 C14 1.1(2)
O3 C14 C13 C12 179.22(19)
O2 C14 C13 C12 -0.5(2)
C6 C5 C4 C3 0.4(3)
C1 C2 C3 C4 0.0(3)
C5 C4 C3 C2 0.0(3)
