#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/15/4021505.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_4021505
loop_
_publ_author_name
'Emma L. Cropper'
'Andrew J. P. White'
'Agnes Ford'
'King Kuok (Mimi) Hii'
_publ_section_title
;
 Ligand Effects in the Synthesis of N-Heterocycles by Intramolecular
 Heck Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1732
_journal_page_last               1735
_journal_paper_doi               10.1021/jo0522660
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.622(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.5637(12)
_cell_length_b                   6.9794(6)
_cell_length_c                   27.0219(18)
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.6924
_cell_measurement_theta_min      3.7777
_cell_volume                     3070.3(4)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 15.9863
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            12773
_diffrn_reflns_theta_full        32.70
_diffrn_reflns_theta_max         32.70
_diffrn_reflns_theta_min         4.25
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         5197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0479P)²+2.3150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1375
_reflns_number_gt                5101
_reflns_number_total             5197
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0522660si20051102_033244_2.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4021505
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.30066(5) 0.00278(13) 0.11825(3) 0.02693(17) Uani 1 1 d .
C2 C 0.38082(6) 0.08578(13) 0.12488(4) 0.02413(18) Uani 1 1 d .
C3 C 0.40953(7) 0.19119(16) 0.16845(4) 0.0315(2) Uani 1 1 d .
H3A H 0.3771 0.2013 0.1939 0.038 Uiso 1 1 calc R
C4 C 0.48543(8) 0.28121(18) 0.17470(5) 0.0389(3) Uani 1 1 d .
H4A H 0.5041 0.3561 0.2039 0.047 Uiso 1 1 calc R
C5 C 0.53401(7) 0.26200(19) 0.13832(5) 0.0397(3) Uani 1 1 d .
H5A H 0.5864 0.3219 0.1428 0.048 Uiso 1 1 calc R
C6 C 0.50589(6) 0.15516(17) 0.09540(4) 0.0328(2) Uani 1 1 d .
H6A H 0.5400 0.1403 0.0710 0.039 Uiso 1 1 calc R
C7 C 0.42838(6) 0.06866(14) 0.08724(4) 0.02535(18) Uani 1 1 d .
C8 C 0.39910(7) -0.03750(16) 0.03922(4) 0.0297(2) Uani 1 1 d .
C9 C 0.42598(8) -0.24403(18) 0.03731(5) 0.0394(3) Uani 1 1 d .
H9A H 0.4834 -0.2557 0.0555 0.047 Uiso 1 1 calc R
H9B H 0.4249 -0.2802 0.0018 0.047 Uiso 1 1 calc R
C10 C 0.37221(9) -0.38452(17) 0.06035(5) 0.0404(3) Uani 1 1 d .
H10A H 0.3991 -0.5118 0.0633 0.049 Uiso 1 1 calc R
H10B H 0.3188 -0.3978 0.0371 0.049 Uiso 1 1 calc R
C11 C 0.35613(8) -0.32480(16) 0.11250(5) 0.0367(2) Uani 1 1 d .
H11A H 0.3443 -0.4404 0.1312 0.044 Uiso 1 1 calc R
H11B H 0.4061 -0.2638 0.1318 0.044 Uiso 1 1 calc R
C12 C 0.28493(7) -0.18697(17) 0.10865(4) 0.0328(2) Uani 1 1 d .
O12 O 0.21395(6) -0.24569(16) 0.09778(4) 0.0511(3) Uani 1 1 d .
C13 C 0.23051(6) 0.13385(18) 0.11417(4) 0.0314(2) Uani 1 1 d .
H13A H 0.1869 0.0889 0.0865 0.038 Uiso 1 1 calc R
H13B H 0.2481 0.2622 0.1047 0.038 Uiso 1 1 calc R
C14 C 0.19426(6) 0.15345(15) 0.16147(4) 0.02579(19) Uani 1 1 d .
C15 C 0.21668(7) 0.03795(16) 0.20335(4) 0.0318(2) Uani 1 1 d .
H15A H 0.2581 -0.0565 0.2036 0.038 Uiso 1 1 calc R
C16 C 0.17910(8) 0.05885(19) 0.24525(5) 0.0377(2) Uani 1 1 d .
H16A H 0.1955 -0.0200 0.2740 0.045 Uiso 1 1 calc R
C17 C 0.11823(8) 0.1936(2) 0.24499(5) 0.0419(3) Uani 1 1 d .
H17A H 0.0919 0.2062 0.2732 0.050 Uiso 1 1 calc R
C18 C 0.09574(9) 0.3098(2) 0.20360(6) 0.0492(3) Uani 1 1 d .
H18A H 0.0539 0.4031 0.2033 0.059 Uiso 1 1 calc R
C19 C 0.13397(8) 0.2913(2) 0.16214(5) 0.0407(3) Uani 1 1 d .
H19A H 0.1187 0.3738 0.1340 0.049 Uiso 1 1 calc R
C20 C 0.35283(8) 0.0499(2) 0.00033(5) 0.0403(3) Uani 1 1 d .
H20A H 0.3382 0.1806 0.0029 0.048 Uiso 1 1 calc R
H20B H 0.3344 -0.0184 -0.0301 0.048 Uiso 1 1 calc R
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
C12 N1 C2 123.87(9)
C12 N1 C13 118.03(9)
C2 N1 C13 117.47(8)
C3 C2 C7 120.50(9)
C3 C2 N1 118.92(9)
C7 C2 N1 120.52(8)
C4 C3 C2 120.10(10)
C5 C4 C3 120.07(11)
C6 C5 C4 119.74(10)
C5 C6 C7 121.44(10)
C6 C7 C2 118.10(9)
C6 C7 C8 119.49(9)
C2 C7 C8 122.42(9)
C20 C8 C7 120.41(10)
C20 C8 C9 122.74(11)
C7 C8 C9 116.84(10)
C8 C9 C10 113.54(10)
C9 C10 C11 114.23(10)
C12 C11 C10 111.97(10)
O12 C12 N1 120.64(12)
O12 C12 C11 120.31(11)
N1 C12 C11 119.04(10)
N1 C13 C14 115.11(9)
C15 C14 C19 118.57(10)
C15 C14 C13 123.31(9)
C19 C14 C13 118.10(10)
C14 C15 C16 120.65(10)
C17 C16 C15 120.15(11)
C18 C17 C16 119.64(11)
C17 C18 C19 120.31(12)
C14 C19 C18 120.66(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C12 1.3653(14)
N1 C2 1.4293(12)
N1 C13 1.4669(13)
C2 C3 1.3956(14)
C2 C7 1.4017(14)
C3 C4 1.3876(16)
C4 C5 1.3868(19)
C5 C6 1.3853(17)
C6 C7 1.3989(14)
C7 C8 1.4952(15)
C8 C20 1.3293(16)
C8 C9 1.5123(16)
C9 C10 1.5318(18)
C10 C11 1.5392(17)
C11 C12 1.5105(17)
C12 O12 1.2285(14)
C13 C14 1.5153(15)
C14 C15 1.3832(15)
C14 C19 1.3892(15)
C15 C16 1.3965(16)
C16 C17 1.3779(19)
C17 C18 1.376(2)
C18 C19 1.3906(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9754754
2 PubChem 11579988
