#------------------------------------------------------------------------------
#$Date: 2022-04-26 17:29:04 +0300 (Tue, 26 Apr 2022) $
#$Revision: 274689 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/22/1552276.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1552276
loop_
_publ_author_name
'Krishnan, G. Anantha'
'Kumar, C. Udhaya'
'Mohandas, T. '
'Pillai, M. Velayutham'
'Sakthivel, P.'
_publ_section_title
;
 Allyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate
;
_journal_coden_ASTM              IUCRBK
_journal_coeditor_code           BV4022
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x190054
_journal_paper_doi               10.1107/S2414314619000543
_journal_volume                  4
_journal_year                    2019
_chemical_formula_iupac          'C17 H16 N2 O3'
_chemical_formula_moiety         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         296.32
_chemical_name_systematic
;
Allyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                108.184(4)
_cell_angle_beta                 103.004(4)
_cell_angle_gamma                105.089(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2151(5)
_cell_length_b                   9.2850(5)
_cell_length_c                   11.6086(7)
_cell_measurement_reflns_used    4207
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.43
_cell_measurement_theta_min      2.47
_cell_volume                     765.64(8)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and  PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3789
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.284
_diffrn_reflns_theta_min         2.472
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            ' orange'
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       ' BLOCK'
_exptl_crystal_F_000             312
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.278
_refine_ls_extinction_coef       0.028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick 2018)
;
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3789
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0520
_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)+(0.0710P)²+0.1156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                2207
_reflns_number_total             3789
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bv4022sup1.cif
_cod_data_source_block           I
_cod_database_code               1552276
_cod_database_fobs_code          1552276
_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, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.13227(16) 0.88787(15) 0.32279(13) 0.0513(4) Uani d 1 . .
O O2 0.72395(18) 0.92452(18) 0.36162(17) 0.0742(5) Uani d 1 . .
O O3 0.62148(18) 1.06948(19) 0.26548(15) 0.0728(5) Uani d 1 . .
N N1 -0.0492(2) 0.7331(2) 0.38698(18) 0.0580(5) Uani d 1 . .
H H1N1 -0.080(3) 0.663(3) 0.4157(19) 0.057(6) Uiso d 1 . .
H H1N2 -0.109(3) 0.797(3) 0.376(2) 0.068(6) Uiso d 1 . .
N N2 0.1936(2) 0.4855(2) 0.48236(19) 0.0700(6) Uani d 1 . .
C C1 0.3644(2) 0.5954(2) 0.21556(18) 0.0474(4) Uani d 1 . .
C C2 0.4475(3) 0.4852(3) 0.2186(2) 0.0693(6) Uani d 1 . .
H H2A 0.523004 0.495812 0.296026 0.083 Uiso calc 1 . .
C C3 0.4174(4) 0.3571(3) 0.1044(3) 0.0938(9) Uani d 1 . .
H H3A 0.472222 0.281595 0.106231 0.113 Uiso calc 1 . .
C C4 0.3083(5) 0.3415(3) -0.0102(3) 0.0942(9) Uani d 1 . .
H H4A 0.290072 0.256420 -0.085936 0.113 Uiso calc 1 . .
C C5 0.2271(4) 0.4499(3) -0.0129(2) 0.0881(8) Uani d 1 . .
H H5A 0.152576 0.439516 -0.090676 0.106 Uiso calc 1 . .
C C6 0.2543(3) 0.5753(3) 0.0988(2) 0.0700(6) Uani d 1 . .
H H6A 0.196780 0.648748 0.095559 0.084 Uiso calc 1 . .
C C7 0.3897(2) 0.7335(2) 0.33875(16) 0.0424(4) Uani d 1 . .
H H7A 0.494936 0.744799 0.405599 0.051 Uiso calc 1 . .
C C8 0.4222(2) 0.8932(2) 0.32389(16) 0.0421(4) Uani d 1 . .
C C9 0.2989(2) 0.9618(2) 0.31696(17) 0.0454(4) Uani d 1 . .
C C10 0.1074(2) 0.7670(2) 0.36705(16) 0.0437(4) Uani d 1 . .
C C11 0.2308(2) 0.6973(2) 0.38400(16) 0.0426(4) Uani d 1 . .
C C12 0.2067(2) 0.5791(2) 0.43693(18) 0.0488(4) Uani d 1 . .
C C13 0.3033(3) 1.1169(3) 0.3039(2) 0.0652(6) Uani d 1 . .
H H13A 0.425021 1.184266 0.324493 0.098 Uiso calc 1 . .
H H13B 0.251375 1.171848 0.361704 0.098 Uiso calc 1 . .
H H13C 0.236508 1.094610 0.217107 0.098 Uiso calc 1 . .
C C14 0.6031(2) 0.9636(2) 0.31985(18) 0.0484(4) Uani d 1 . .
C C15A 0.814(5) 1.136(3) 0.2707(18) 0.084(3) Uani d 0.280(7) A 1
H H15A 0.885611 1.222435 0.354245 0.101 Uiso calc 0.280(7) A 1
H H15B 0.864085 1.051113 0.257234 0.101 Uiso calc 0.280(7) A 1
C C16A 0.8150(18) 1.1965(15) 0.1739(11) 0.098(3) Uani d 0.280(7) A 1
H H16A 0.885497 1.304306 0.198254 0.117 Uiso calc 0.280(7) A 1
C C17A 0.728(2) 1.1155(18) 0.0576(11) 0.149(5) Uani d 0.280(7) A 1
H H17A 0.656193 1.007380 0.029871 0.179 Uiso calc 0.280(7) A 1
H H17B 0.734994 1.163255 -0.001548 0.179 Uiso calc 0.280(7) A 1
C C15B 0.7942(19) 1.1526(13) 0.2641(6) 0.093(2) Uani d 0.720(7) A 2
H H15C 0.824470 1.268629 0.307193 0.111 Uiso calc 0.720(7) A 2
H H15D 0.882796 1.122081 0.311836 0.111 Uiso calc 0.720(7) A 2
C C16B 0.8014(7) 1.1178(6) 0.1398(4) 0.1014(17) Uani d 0.720(7) A 2
H H16B 0.721066 1.016544 0.079943 0.122 Uiso calc 0.720(7) A 2
C C17B 0.8942(6) 1.1959(7) 0.0949(5) 0.1199(19) Uani d 0.720(7) A 2
H H17C 0.978344 1.298620 0.147859 0.144 Uiso calc 0.720(7) A 2
H H17D 0.880257 1.152447 0.007964 0.144 Uiso calc 0.720(7) 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C10 O1 C9 . . 119.93(13)
C14 O3 C15B . . 120.1(4)
C14 O3 C15A . . 110.7(7)
C10 N1 H1N1 . . 120.4(14)
C10 N1 H1N2 . . 116.0(14)
H1N1 N1 H1N2 . . 123(2)
C2 C1 C6 . . 118.3(2)
C2 C1 C7 . . 120.80(19)
C6 C1 C7 . . 120.86(16)
C1 C2 C3 . . 119.4(2)
C1 C2 H2A . . 120.3
C3 C2 H2A . . 120.3
C4 C3 C2 . . 120.8(2)
C4 C3 H3A . . 119.6
C2 C3 H3A . . 119.6
C5 C4 C3 . . 119.7(2)
C5 C4 H4A . . 120.1
C3 C4 H4A . . 120.1
C4 C5 C6 . . 120.1(3)
C4 C5 H5A . . 120.0
C6 C5 H5A . . 120.0
C5 C6 C1 . . 121.7(2)
C5 C6 H6A . . 119.1
C1 C6 H6A . . 119.1
C8 C7 C11 . . 109.31(13)
C8 C7 C1 . . 112.26(14)
C11 C7 C1 . . 111.41(14)
C8 C7 H7A . . 107.9
C11 C7 H7A . . 107.9
C1 C7 H7A . . 107.9
C9 C8 C14 . . 124.63(16)
C9 C8 C7 . . 122.28(15)
C14 C8 C7 . . 113.08(15)
C8 C9 O1 . . 120.91(15)
C8 C9 C13 . . 131.04(17)
O1 C9 C13 . . 108.05(15)
N1 C10 C11 . . 128.55(17)
N1 C10 O1 . . 110.40(15)
C11 C10 O1 . . 121.05(15)
C10 C11 C12 . . 119.89(15)
C10 C11 C7 . . 121.69(15)
C12 C11 C7 . . 118.27(14)
N2 C12 C11 . . 177.5(2)
C9 C13 H13A . . 109.5
C9 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C9 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
O2 C14 O3 . . 122.49(17)
O2 C14 C8 . . 121.74(17)
O3 C14 C8 . . 115.75(16)
C16A C15A O3 . . 108(2)
C16A C15A H15A . . 110.1
O3 C15A H15A . . 110.1
C16A C15A H15B . . 110.1
O3 C15A H15B . . 110.1
H15A C15A H15B . . 108.4
C17A C16A C15A . . 124.5(11)
C17A C16A H16A . . 117.7
C15A C16A H16A . . 117.7
C16A C17A H17A . . 120.0
C16A C17A H17B . . 120.0
H17A C17A H17B . . 120.0
C16B C15B O3 . . 112.7(8)
C16B C15B H15C . . 109.1
O3 C15B H15C . . 109.1
C16B C15B H15D . . 109.1
O3 C15B H15D . . 109.1
H15C C15B H15D . . 107.8
C17B C16B C15B . . 131.9(8)
C17B C16B H16B . . 114.0
C15B C16B H16B . . 114.0
C16B C17B H17C . . 120.0
C16B C17B H17D . . 120.0
H17C C17B H17D . . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C10 . 1.361(2)
O1 C9 . 1.389(2)
O2 C14 . 1.197(2)
O3 C14 . 1.319(2)
O3 C15B . 1.434(13)
O3 C15A . 1.52(4)
N1 C10 . 1.333(2)
N1 H1N1 . 0.83(2)
N1 H1N2 . 0.88(2)
N2 C12 . 1.143(2)
C1 C2 . 1.375(3)
C1 C6 . 1.376(3)
C1 C7 . 1.521(2)
C2 C3 . 1.396(4)
C2 H2A . 0.9300
C3 C4 . 1.367(4)
C3 H3A . 0.9300
C4 C5 . 1.349(4)
C4 H4A . 0.9300
C5 C6 . 1.371(3)
C5 H5A . 0.9300
C6 H6A . 0.9300
C7 C8 . 1.508(2)
C7 C11 . 1.511(2)
C7 H7A . 0.9800
C8 C9 . 1.331(2)
C8 C14 . 1.477(2)
C9 C13 . 1.486(2)
C10 C11 . 1.348(2)
C11 C12 . 1.409(2)
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
C15A C16A . 1.404(4)
C15A H15A . 0.9700
C15A H15B . 0.9700
C16A C17A . 1.245(4)
C16A H16A . 0.9300
C17A H17A . 0.9300
C17A H17B . 0.9300
C15B C16B . 1.395(4)
C15B H15C . 0.9700
C15B H15D . 0.9700
C16B C17B . 1.227(3)
C16B H16B . 0.9300
C17B H17C . 0.9300
C17B H17D . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N1 N2 2_566 0.83(2) 2.24(2) 3.051(2) 166.0(19) yes
N1 H1N2 O2 1_455 0.88(2) 2.04(2) 2.919(2) 171(2) yes
C13 H13A O3 . 0.96 2.27 2.868(3) 119.7 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . . . . -0.2(3)
C7 C1 C2 C3 . . . . 178.11(18)
C1 C2 C3 C4 . . . . 0.8(4)
C2 C3 C4 C5 . . . . -0.7(4)
C3 C4 C5 C6 . . . . 0.1(4)
C4 C5 C6 C1 . . . . 0.4(4)
C2 C1 C6 C5 . . . . -0.4(3)
C7 C1 C6 C5 . . . . -178.71(19)
C2 C1 C7 C8 . . . . 135.66(18)
C6 C1 C7 C8 . . . . -46.0(2)
C2 C1 C7 C11 . . . . -101.37(19)
C6 C1 C7 C11 . . . . 76.9(2)
C11 C7 C8 C9 . . . . -17.1(2)
C1 C7 C8 C9 . . . . 106.99(19)
C11 C7 C8 C14 . . . . 162.07(14)
C1 C7 C8 C14 . . . . -73.79(18)
C14 C8 C9 O1 . . . . -179.35(15)
C7 C8 C9 O1 . . . . -0.2(3)
C14 C8 C9 C13 . . . . 0.1(3)
C7 C8 C9 C13 . . . . 179.25(19)
C10 O1 C9 C8 . . . . 16.3(2)
C10 O1 C9 C13 . . . . -163.28(16)
C9 O1 C10 N1 . . . . 168.74(16)
C9 O1 C10 C11 . . . . -11.9(2)
N1 C10 C11 C12 . . . . -4.5(3)
O1 C10 C11 C12 . . . . 176.32(16)
N1 C10 C11 C7 . . . . 171.01(18)
O1 C10 C11 C7 . . . . -8.2(3)
C8 C7 C11 C10 . . . . 21.4(2)
C1 C7 C11 C10 . . . . -103.26(19)
C8 C7 C11 C12 . . . . -163.08(15)
C1 C7 C11 C12 . . . . 72.3(2)
C15B O3 C14 O2 . . . . -5.2(5)
C15A O3 C14 O2 . . . . -2.7(9)
C15B O3 C14 C8 . . . . 176.0(4)
C15A O3 C14 C8 . . . . 178.4(9)
C9 C8 C14 O2 . . . . 158.52(19)
C7 C8 C14 O2 . . . . -20.7(2)
C9 C8 C14 O3 . . . . -22.6(3)
C7 C8 C14 O3 . . . . 158.17(15)
C14 O3 C15A C16A . . . . 158.0(12)
O3 C15A C16A C17A . . . . -56(3)
C14 O3 C15B C16B . . . . 117.5(6)
O3 C15B C16B C17B . . . . 152.6(7)
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-04-26T17:25:00+03:00
'Updated bibliographic information.'
