#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:29:48 +0300 (Fri, 05 May 2023) $
#$Revision: 283493 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159047.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_7159047
loop_
_publ_author_name
'Obydennov, Dmitrii L.'
'Simbirtseva, Alena E.'
'Shirinkin, Alexander S.'
'Kornev, Mikhail Y.'
'Sosnovskikh, Vyacheslav Y.'
_publ_section_title
;
 A novel strategy for the functionalization and design of
 4-methylene-4H-pyran merocyanines via enamination and
 1,8-conjugate addition.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              600
_journal_page_last               620
_journal_paper_doi               10.1039/d2ob01862d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-10 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.260(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3597(8)
_cell_length_b                   18.0931(15)
_cell_length_c                   7.4440(8)
_cell_measurement_reflns_used    1963
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.4110
_cell_measurement_theta_min      4.0280
_cell_volume                     1253.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  67.00   1.00   30.00    --   21.45  25.00  60.00   34
  2  ω    -50.00  52.00   1.00   30.00    --   21.45 -25.00-103.00  102
  3  ω    -26.00  -1.00   1.00   30.00    --  -23.01  25.00  60.00   25
  4  ω    -73.00 -47.00   1.00   30.00    --  -23.01 -25.00-103.00   26
  5  ω     40.00  95.00   1.00   30.00    --   21.45 178.00-120.00   55
  6  ω    -91.00 -37.00   1.00   30.00    --  -23.01 -57.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0604768000
_diffrn_orient_matrix_UB_12      -0.0121611000
_diffrn_orient_matrix_UB_13      0.0417423000
_diffrn_orient_matrix_UB_21      0.0390521000
_diffrn_orient_matrix_UB_22      0.0049028000
_diffrn_orient_matrix_UB_23      0.0862844000
_diffrn_orient_matrix_UB_31      -0.0251487000
_diffrn_orient_matrix_UB_32      0.0369192000
_diffrn_orient_matrix_UB_33      0.0022818000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.472
_diffrn_reflns_theta_min         3.868
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'greenish brown'
_exptl_crystal_colour_modifier   green
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.004(3)
_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   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1391
_refine_ls_R_factor_gt           0.0694
_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)+(0.1100P)²+0.0250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.2367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1608
_reflns_number_total             3371
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01862d2.cif
_cod_data_source_block           exp_22
_cod_depositor_comments          'Adding full bibliography for 7159047.cif.'
_cod_database_code               7159047
_shelx_shelxl_version_number     2018/3
_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   0.979
_shelx_estimated_absorpt_t_min   0.962
_reflns_odcompleteness_completeness 98.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.379
_oxdiff_exptl_absorpt_empirical_full_min 0.818
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62931(16) 0.30147(8) 0.6988(2) 0.0589(5) Uani 1 1 d . . . . .
N1 N 0.9106(2) 0.14434(11) 0.5807(3) 0.0702(6) Uani 1 1 d . . . . .
C2 C 0.5302(2) 0.34857(13) 0.7555(3) 0.0552(6) Uani 1 1 d . . . . .
C5 C 0.7668(3) 0.40318(13) 0.6154(3) 0.0558(6) Uani 1 1 d . . . . .
C6 C 0.7503(2) 0.32875(13) 0.6328(3) 0.0542(6) Uani 1 1 d . . . . .
C4 C 0.6648(2) 0.45347(12) 0.6671(3) 0.0537(6) Uani 1 1 d . . . . .
C3 C 0.5450(2) 0.42148(14) 0.7438(3) 0.0566(6) Uani 1 1 d . . . . .
C8 C 0.8248(3) 0.20098(13) 0.6136(3) 0.0600(6) Uani 1 1 d . . . . .
C7 C 0.8486(3) 0.27368(13) 0.5890(3) 0.0587(6) Uani 1 1 d . . . . .
C11 C 0.6753(3) 0.53011(13) 0.6457(3) 0.0589(6) Uani 1 1 d . . . . .
N2 N 0.4906(3) 0.61751(13) 0.7622(4) 0.0886(8) Uani 1 1 d . . . . .
C12 C 0.5743(3) 0.57874(13) 0.7090(4) 0.0637(6) Uani 1 1 d . . . . .
C1 C 0.4096(3) 0.30766(13) 0.8238(4) 0.0735(8) Uani 1 1 d . . . . .
H1A H 0.360631 0.278946 0.727525 0.110 Uiso 1 1 calc R U . . .
H1B H 0.343632 0.342175 0.867605 0.110 Uiso 1 1 calc R U . . .
H1C H 0.446558 0.275433 0.920258 0.110 Uiso 1 1 calc R U . . .
C13 C 0.7842(3) 0.56224(13) 0.5529(4) 0.0673(7) Uani 1 1 d . . . . .
N3 N 0.8709(3) 0.58852(15) 0.4753(4) 0.1014(10) Uani 1 1 d . . . . .
C10 C 0.8700(3) 0.06905(14) 0.6138(4) 0.0811(9) Uani 1 1 d . . . . .
H10A H 0.938306 0.047642 0.704552 0.122 Uiso 1 1 calc R U . . .
H10B H 0.868338 0.041033 0.504053 0.122 Uiso 1 1 calc R U . . .
H10C H 0.776205 0.068385 0.654734 0.122 Uiso 1 1 calc R U . . .
C9 C 1.0492(3) 0.15612(17) 0.5138(5) 0.0881(9) Uani 1 1 d . . . . .
H9A H 1.035664 0.182704 0.401650 0.132 Uiso 1 1 calc R U . . .
H9B H 1.093175 0.109237 0.494959 0.132 Uiso 1 1 calc R U . . .
H9C H 1.110105 0.184199 0.600750 0.132 Uiso 1 1 calc R U . . .
H5 H 0.855(3) 0.4195(12) 0.565(3) 0.059(6) Uiso 1 1 d . . . . .
H8 H 0.732(3) 0.1831(12) 0.656(3) 0.062(7) Uiso 1 1 d . . . . .
H3 H 0.474(3) 0.4511(12) 0.789(3) 0.067(7) Uiso 1 1 d . . . . .
H7 H 0.935(3) 0.2920(13) 0.534(4) 0.082(8) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C6 120.15(18) . . ?
C8 N1 C10 121.1(2) . . ?
C8 N1 C9 121.6(2) . . ?
C10 N1 C9 117.3(2) . . ?
O1 C2 C1 111.31(19) . . ?
C3 C2 O1 121.5(2) . . ?
C3 C2 C1 127.2(2) . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 116.0(13) . . ?
C4 C5 H5 122.1(13) . . ?
O1 C6 C7 114.3(2) . . ?
C5 C6 O1 119.7(2) . . ?
C5 C6 C7 126.1(2) . . ?
C5 C4 C3 115.6(2) . . ?
C11 C4 C5 123.6(2) . . ?
C11 C4 C3 120.8(2) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 117.3(15) . . ?
C4 C3 H3 121.5(15) . . ?
N1 C8 C7 127.5(2) . . ?
N1 C8 H8 111.5(13) . . ?
C7 C8 H8 121.0(13) . . ?
C6 C7 H7 115.8(14) . . ?
C8 C7 C6 122.2(2) . . ?
C8 C7 H7 122.0(14) . . ?
C4 C11 C12 121.5(2) . . ?
C4 C11 C13 121.7(2) . . ?
C12 C11 C13 116.8(2) . . ?
N2 C12 C11 178.8(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C13 C11 178.9(3) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.360(3) . ?
O1 C6 1.374(3) . ?
N1 C8 1.341(3) . ?
N1 C10 1.443(3) . ?
N1 C9 1.455(4) . ?
C2 C3 1.330(3) . ?
C2 C1 1.485(3) . ?
C5 C6 1.363(3) . ?
C5 C4 1.403(3) . ?
C5 H5 0.99(2) . ?
C6 C7 1.419(3) . ?
C4 C3 1.435(3) . ?
C4 C11 1.400(3) . ?
C3 H3 0.94(2) . ?
C8 C7 1.350(3) . ?
C8 H8 1.01(3) . ?
C7 H7 1.00(3) . ?
C11 C12 1.410(3) . ?
C11 C13 1.417(3) . ?
N2 C12 1.153(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C13 N3 1.149(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 1.3(4) . . . . ?
O1 C6 C7 C8 -1.0(3) . . . . ?
N1 C8 C7 C6 -178.6(2) . . . . ?
C2 O1 C6 C5 -3.5(3) . . . . ?
C2 O1 C6 C7 176.30(19) . . . . ?
C5 C6 C7 C8 178.8(2) . . . . ?
C5 C4 C3 C2 -3.1(3) . . . . ?
C5 C4 C11 C12 -176.4(2) . . . . ?
C5 C4 C11 C13 6.3(4) . . . . ?
C6 O1 C2 C3 2.1(3) . . . . ?
C6 O1 C2 C1 -179.2(2) . . . . ?
C6 C5 C4 C3 1.7(3) . . . . ?
C6 C5 C4 C11 -177.7(2) . . . . ?
C4 C5 C6 O1 1.5(3) . . . . ?
C4 C5 C6 C7 -178.2(2) . . . . ?
C3 C4 C11 C12 4.2(4) . . . . ?
C3 C4 C11 C13 -173.1(2) . . . . ?
C11 C4 C3 C2 176.3(2) . . . . ?
C1 C2 C3 C4 -177.2(2) . . . . ?
C10 N1 C8 C7 -179.9(3) . . . . ?
C9 N1 C8 C7 1.3(4) . . . . ?
