#------------------------------------------------------------------------------
#$Date: 2022-02-25 03:37:20 +0200 (Fri, 25 Feb 2022) $
#$Revision: 273152 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158538.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_7158538
loop_
_publ_author_name
'Suresh, Alati'
'Lal, Sohan'
'Namboothiri, Irishi N.'
_publ_section_title
;
 Regio- and stereoselective synthesis of functionalized and fused
 heterocycles from Morita-Baylis-Hillman adducts of dicyclopentadienone
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB02505H
_journal_year                    2022
_chemical_formula_moiety         'C18 H16 N2'
_chemical_formula_sum            'C18 H16 N2'
_chemical_formula_weight         260.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-02-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-12 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.892(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3943(2)
_cell_length_b                   18.0605(5)
_cell_length_c                   11.5544(4)
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      24.7590
_cell_measurement_theta_min      2.2390
_cell_volume                     1318.31(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ   -158.68  65.32   1.00    1.00  86.05  -4.81  31.50    --   224
  2  ω   -100.47  23.53   1.00    1.00    --   -4.81 -59.25  20.08  124
  3  ω   -100.47  23.53   1.00    1.00    --   -4.81 -59.25  92.08  124
  4  φ    -25.73 158.27   1.00    1.00  17.58  -4.81 -31.50    --   184
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0077451000
_diffrn_orient_matrix_UB_12      0.0207556000
_diffrn_orient_matrix_UB_13      -0.0525931000
_diffrn_orient_matrix_UB_21      -0.0110467000
_diffrn_orient_matrix_UB_22      0.0330027000
_diffrn_orient_matrix_UB_23      0.0317540000
_diffrn_orient_matrix_UB_31      0.1115123000
_diffrn_orient_matrix_UB_32      0.0046957000
_diffrn_orient_matrix_UB_33      0.0091608000
_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  0.1382
_diffrn_reflns_av_unetI/netI     0.1307
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28488
_diffrn_reflns_theta_full        24.9800
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.11
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3116
_exptl_crystal_description       block
_exptl_crystal_F_000             552.1981
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.2922
_refine_diff_density_min         -0.3290
_refine_diff_density_rms         0.0782
_refine_ls_d_res_high            0.8415
_refine_ls_d_res_low             9.6496
_refine_ls_goodness_of_fit_ref   1.0366
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0366
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0647P)²+0.0521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              -5
_reflns_number_gt                1605
_reflns_number_total             2326
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ob02505h2.cif
_cod_data_source_block           INN_AS_RETRO_AMIDINE_autored
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7158538
_reflns_odcompleteness_completeness 87.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.81
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00g)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00e,H00f)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00C(H00C), C00G(H00h), C00H(H00i), C00I(H00j),
 C00J(H00k), C00K(H00l)
;
_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 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.797
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
N001 N 0.6674(2) 0.71232(8) 0.31661(13) 0.0231(4) Uani 1.000000 .
N002 N 0.6670(2) 0.65101(9) 0.50073(14) 0.0285(4) Uani 1.000000 .
C00A C 1.1663(3) 0.81998(10) 0.39012(17) 0.0257(5) Uani 1.000000 .
H00A H 1.2995(3) 0.80962(10) 0.35766(17) 0.0309(6) Uiso 1.000000 R
C00B C 0.9692(3) 0.79854(10) 0.29827(17) 0.0247(5) Uani 1.000000 .
H00B H 1.0131(3) 0.77615(10) 0.22661(17) 0.0297(6) Uiso 1.000000 R
C00C C 0.9392(3) 0.91562(10) 0.45901(19) 0.0287(5) Uani 1.000000 .
H00C H 0.9350(3) 0.93187(10) 0.53681(19) 0.0345(6) Uiso 1.000000 R
C00D C 1.1369(3) 0.90504(10) 0.40296(17) 0.0269(5) Uani 1.000000 .
H00D H 1.2650(3) 0.93305(10) 0.43975(17) 0.0323(6) Uiso 1.000000 R
C00E C 1.0499(3) 0.92563(11) 0.27576(18) 0.0289(5) Uani 1.000000 .
H00e H 1.0115(3) 0.97862(11) 0.26603(18) 0.0347(6) Uiso 1.000000 R
H00f H 1.1458(3) 0.91122(11) 0.22005(18) 0.0347(6) Uiso 1.000000 R
C00F C 0.8562(3) 0.87469(10) 0.26984(18) 0.0285(5) Uani 1.000000 .
H00g H 0.7524(3) 0.87689(10) 0.19575(18) 0.0342(6) Uiso 1.000000 R
C00G C 0.7740(3) 0.89816(10) 0.38014(19) 0.0304(5) Uani 1.000000 .
H00h H 0.6297(3) 0.90001(10) 0.39082(19) 0.0365(6) Uiso 1.000000 R
C00H C 0.0891(3) 0.61145(11) 0.1846(2) 0.0353(5) Uani 1.000000 .
H00i H 0.0203(3) 0.62350(11) 0.1081(2) 0.0424(6) Uiso 1.000000 R
C00I C 0.2907(3) 0.57619(11) 0.40759(19) 0.0336(5) Uani 1.000000 .
H00j H 0.3583(3) 0.56388(11) 0.48425(19) 0.0403(6) Uiso 1.000000 R
C00J C 0.0000(3) 0.56004(12) 0.2508(2) 0.0391(6) Uani 1.000000 .
H00k H -0.1307(3) 0.53711(12) 0.2204(2) 0.0469(7) Uiso 1.000000 R
C00K C 0.1019(3) 0.54216(12) 0.3615(2) 0.0408(6) Uani 1.000000 .
H00l H 0.0419(3) 0.50614(12) 0.4065(2) 0.0490(7) Uiso 1.000000 R
C003 C 0.5846(3) 0.66593(10) 0.38894(17) 0.0230(5) Uani 1.000000 .
C004 C 0.8519(3) 0.74362(10) 0.36145(17) 0.0214(4) Uani 1.000000 .
C005 C 0.9539(3) 0.73050(10) 0.47526(17) 0.0227(5) Uani 1.000000 .
C006 C 0.3819(3) 0.62855(10) 0.34167(16) 0.0241(5) Uani 1.000000 .
C007 C 1.1591(3) 0.77227(11) 0.50152(18) 0.0257(5) Uani 1.000000 .
H00m H 1.282(3) 0.7391(10) 0.5157(16) 0.025(5) Uiso 1.000000 .
H00n H 1.168(3) 0.8026(11) 0.5724(17) 0.031(5) Uiso 1.000000 .
C008 C 0.8514(3) 0.68389(11) 0.54281(17) 0.0288(5) Uani 1.000000 .
H008 H 0.9134(3) 0.67479(11) 0.62166(17) 0.0346(6) Uiso 1.000000 R
C009 C 0.2787(3) 0.64554(11) 0.22946(17) 0.0275(5) Uani 1.000000 .
H009 H 0.3389(3) 0.68083(11) 0.18329(17) 0.0329(6) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C004 N001 C003 115.46(16) . . ?
C008 N002 C003 116.83(16) . . ?
C00D C00A C00B 102.24(15) . . ?
C007 C00A C00B 107.46(14) . . ?
C007 C00A C00D 116.62(16) . . ?
C00F C00B C00A 102.83(14) . . ?
C004 C00B C00A 104.14(15) . . ?
C004 C00B C00F 115.76(15) . . ?
C00G C00C C00D 107.78(18) . . ?
C00C C00D C00A 106.58(15) . . ?
C00E C00D C00A 100.31(15) . . ?
C00E C00D C00C 100.11(15) . . ?
C00F C00E C00D 93.89(15) . . ?
C00E C00F C00B 100.05(14) . . ?
C00G C00F C00B 106.19(16) . . ?
C00G C00F C00E 100.24(15) . . ?
C00F C00G C00C 107.61(17) . . ?
C009 C00H C00J 120.2(2) . . ?
C006 C00I C00K 120.2(2) . . ?
C00K C00J C00H 119.6(2) . . ?
C00J C00K C00I 120.7(2) . . ?
N002 C003 N001 125.91(17) . . ?
C006 C003 N001 117.24(17) . . ?
C006 C003 N002 116.85(16) . . ?
C00B C004 N001 124.62(17) . . ?
C005 C004 N001 123.29(17) . . ?
C005 C004 C00B 112.05(16) . . ?
C007 C005 C004 111.80(16) . . ?
C008 C005 C004 116.30(17) . . ?
C008 C005 C007 131.89(18) . . ?
C003 C006 C00I 121.34(18) . . ?
C009 C006 C00I 118.58(18) . . ?
C009 C006 C003 120.08(17) . . ?
C005 C007 C00A 104.34(15) . . ?
C005 C008 N002 122.15(18) . . ?
C006 C009 C00H 120.67(19) . . ?
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
N001 C003 1.348(2) . ?
N001 C004 1.338(2) . ?
N002 C003 1.345(2) . ?
N002 C008 1.342(2) . ?
C00A C00B 1.566(3) . ?
C00A C00D 1.558(3) . ?
C00A C007 1.556(3) . ?
C00B C00F 1.564(3) . ?
C00B C004 1.499(2) . ?
C00C C00D 1.519(3) . ?
C00C C00G 1.322(3) . ?
C00D C00E 1.535(3) . ?
C00E C00F 1.536(3) . ?
C00F C00G 1.513(3) . ?
C00H C00J 1.381(3) . ?
C00H C009 1.387(3) . ?
C00I C00K 1.386(3) . ?
C00I C006 1.397(3) . ?
C00J C00K 1.381(3) . ?
C003 C006 1.488(3) . ?
C004 C005 1.395(3) . ?
C005 C007 1.503(3) . ?
C005 C008 1.380(3) . ?
C006 C009 1.395(3) . ?
