#------------------------------------------------------------------------------
#$Date: 2022-12-06 10:48:14 +0200 (Tue, 06 Dec 2022) $
#$Revision: 279729 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106337.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_8106337
loop_
_publ_author_name
'Li, Da'
'Zhou, Yan'
'Zhong, Wei'
'Peng, Ling'
_publ_section_title
;
 Crystal structure of
 2-amino-5-oxo-4-(4-chloro-phenyl)-4,5,6,7-tetrahydro-cyclopenta[b]pyran-3-carbonitrile,
 C15H11ClN2O2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              899
_journal_page_last               900
_journal_paper_doi               10.1515/ncrs-2018-0087
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C15 H11 Cl N2 O2'
_chemical_formula_sum            'C15 H11 Cl N2 O2'
_chemical_formula_weight         286.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 102.415(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.955(7)
_cell_length_b                   10.425(7)
_cell_length_c                   20.149(13)
_cell_measurement_reflns_used    2187
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      2.53
_cell_volume                     2658(3)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6549
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.070
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9417
_exptl_absorpt_correction_T_min  0.9285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0361
_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)+(0.0404P)²+0.9489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0917
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1813
_reflns_number_total             2328
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0087_suppl.cif
_cod_data_source_block           a
_cod_database_code               8106337
_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_max   0.942
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_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
N1 N 0.40831(13) -0.08472(17) 0.49442(10) 0.0652(5) Uani 1 1 d . . . . .
N2 N 0.38399(11) 0.25049(15) 0.43688(8) 0.0540(4) Uani 1 1 d . . . . .
H2A H 0.438827 0.206820 0.455673 0.065 Uiso 1 1 calc R . . . .
H2B H 0.390766 0.328919 0.425288 0.065 Uiso 1 1 calc R . . . .
C1 C 0.14267(14) -0.29775(18) 0.28576(10) 0.0498(5) Uani 1 1 d . . . . .
C2 C 0.15125(15) -0.32151(18) 0.35386(11) 0.0564(5) Uani 1 1 d . . . . .
H2 H 0.156579 -0.405151 0.370297 0.068 Uiso 1 1 calc R . . . .
C3 C 0.15183(15) -0.21899(17) 0.39753(10) 0.0502(5) Uani 1 1 d . . . . .
H3 H 0.157048 -0.234528 0.443588 0.060 Uiso 1 1 calc R . . . .
C4 C 0.14482(12) -0.09389(15) 0.37416(9) 0.0383(4) Uani 1 1 d . . . . .
C5 C 0.13709(14) -0.07347(17) 0.30547(9) 0.0484(5) Uani 1 1 d . . . . .
H5 H 0.132841 0.010033 0.288852 0.058 Uiso 1 1 calc R . . . .
C6 C 0.13556(15) -0.17488(19) 0.26097(10) 0.0537(5) Uani 1 1 d . . . . .
H6 H 0.129775 -0.159865 0.214818 0.064 Uiso 1 1 calc R . . . .
C7 C 0.15226(12) 0.01796(16) 0.42388(9) 0.0404(4) Uani 1 1 d . . . . .
H7 H 0.134466 -0.013128 0.465938 0.049 Uiso 1 1 calc R . . . .
C8 C 0.26338(13) 0.07436(16) 0.44074(8) 0.0405(4) Uani 1 1 d . . . . .
C9 C 0.34554(14) -0.01045(18) 0.47073(9) 0.0470(5) Uani 1 1 d . . . . .
C10 C 0.28815(13) 0.19641(17) 0.42569(8) 0.0415(4) Uani 1 1 d . . . . .
C11 C 0.10983(13) 0.24216(16) 0.38367(9) 0.0414(4) Uani 1 1 d . . . . .
C12 C 0.07892(13) 0.12499(16) 0.39616(9) 0.0412(4) Uani 1 1 d . . . . .
C13 C -0.03618(14) 0.12100(18) 0.37821(10) 0.0498(5) Uani 1 1 d . . . . .
C14 C -0.07477(15) 0.24969(18) 0.34637(12) 0.0595(5) Uani 1 1 d . . . . .
H14A H -0.125975 0.287439 0.369336 0.071 Uiso 1 1 calc R . . . .
H14B H -0.107384 0.239285 0.298632 0.071 Uiso 1 1 calc R . . . .
C15 C 0.02440(14) 0.33452(18) 0.35508(10) 0.0520(5) Uani 1 1 d . . . . .
H15A H 0.033161 0.368696 0.311853 0.062 Uiso 1 1 calc R . . . .
H15B H 0.021876 0.404852 0.386213 0.062 Uiso 1 1 calc R . . . .
Cl1 Cl 0.14294(5) -0.42584(5) 0.23024(3) 0.0780(2) Uani 1 1 d . . . . .
O1 O -0.09200(10) 0.03086(13) 0.38695(9) 0.0701(5) Uani 1 1 d . . . . .
O2 O 0.21221(9) 0.28365(11) 0.39566(6) 0.0467(3) Uani 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 Cl1 119.45(16) . .
C6 C1 C2 121.10(18) . .
C6 C1 Cl1 119.44(17) . .
C1 C2 C3 118.93(18) . .
C2 C3 C4 121.40(18) . .
C3 C4 C7 120.44(16) . .
C5 C4 C3 118.13(16) . .
C5 C4 C7 121.33(15) . .
C4 C5 C6 121.26(17) . .
C1 C6 C5 119.17(19) . .
C8 C7 C4 111.36(14) . .
C12 C7 C4 112.32(14) . .
C12 C7 C8 106.83(14) . .
C9 C8 C7 116.22(15) . .
C10 C8 C7 124.54(15) . .
C10 C8 C9 119.14(15) . .
N1 C9 C8 176.24(19) . .
N2 C10 C8 127.63(16) . .
N2 C10 O2 110.15(15) . .
C8 C10 O2 122.22(15) . .
C12 C11 C15 116.11(16) . .
C12 C11 O2 125.40(16) . .
O2 C11 C15 118.49(15) . .
C11 C12 C7 124.41(16) . .
C11 C12 C13 108.29(16) . .
C13 C12 C7 127.30(15) . .
C12 C13 C14 107.75(15) . .
O1 C13 C12 126.31(18) . .
O1 C13 C14 125.94(17) . .
C13 C14 C15 105.52(15) . .
C11 C15 C14 101.87(15) . .
C11 O2 C10 116.25(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C9 1.150(2) .
N2 C10 1.338(2) .
C1 C2 1.375(3) .
C1 C6 1.371(3) .
C1 Cl1 1.742(2) .
C2 C3 1.383(3) .
C3 C4 1.383(2) .
C4 C5 1.383(3) .
C4 C7 1.527(2) .
C5 C6 1.384(3) .
C7 C8 1.524(2) .
C7 C12 1.494(2) .
C8 C9 1.415(3) .
C8 C10 1.362(2) .
C10 O2 1.380(2) .
C11 C12 1.326(2) .
C11 C15 1.487(3) .
C11 O2 1.366(2) .
C12 C13 1.457(3) .
C13 C14 1.524(3) .
C13 O1 1.221(2) .
C14 C15 1.538(3) .
