#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/55/4025520.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_4025520
loop_
_publ_author_name
'Bangben Yao'
'Yuhong Zhang'
'Yong Li'
_publ_section_title
;
 Copper-Catalyzed Coupling Reaction of C-OMe Bonds Adjacent to a Nitrogen
 Atom with Terminal Alkynes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4554
_journal_page_last               4561
_journal_paper_doi               10.1021/jo1007898
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C23 H22 N O2'
_chemical_formula_sum            'C23 H22 N O2'
_chemical_formula_weight         344.42
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 93.673(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.89032(15)
_cell_length_b                   18.6263(5)
_cell_length_c                   8.9648(2)
_cell_measurement_reflns_used    3065
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.8876
_cell_measurement_theta_min      2.3699
_cell_volume                     981.55(4)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_molecular_graphics
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5209
_diffrn_reflns_theta_full        66.99
_diffrn_reflns_theta_max         66.99
_diffrn_reflns_theta_min         4.75
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(3)
_refine_ls_extinction_coef       0.0072(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2589
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0346
_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)+(0.0589P)²+0.0658P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                2285
_reflns_number_total             2589
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1007898_si_001.cif
_cod_data_source_block           091208_YBB091208
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        981.56(4)
_cod_database_code               4025520
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C -0.0104(4) 0.31869(12) 0.7732(2) 0.0526(5) Uani 1 1 d . . .
C8 C 0.1358(3) 0.50090(12) 0.7563(2) 0.0514(5) Uani 1 1 d . . .
C7 C 0.0330(3) 0.55594(11) 0.7466(2) 0.0519(5) Uani 1 1 d . . .
C9 C 0.2626(3) 0.43335(11) 0.7879(2) 0.0470(4) Uani 1 1 d . . .
O2 O 0.7151(3) 0.37159(9) 0.45959(19) 0.0697(5) Uani 1 1 d . . .
C12 C -0.1390(3) 0.25326(12) 0.7641(2) 0.0515(5) Uani 1 1 d . . .
C10 C 0.1057(3) 0.37153(12) 0.7803(2) 0.0511(5) Uani 1 1 d . . .
N1 N 0.3854(3) 0.43392(11) 0.93680(18) 0.0539(4) Uani 1 1 d . . .
H1 H 0.4542 0.3904 0.9495 0.065 Uiso 1 1 calc R . .
C20 C 0.6463(4) 0.43967(15) 0.4496(2) 0.0578(5) Uani 1 1 d . . .
C6 C -0.0953(3) 0.62212(11) 0.7453(2) 0.0493(5) Uani 1 1 d . . .
C16 C -0.4566(4) 0.18124(16) 0.8267(3) 0.0719(7) Uani 1 1 d . . .
H16 H -0.5905 0.1761 0.8752 0.086 Uiso 1 1 calc R . .
C13 C -0.0599(4) 0.19542(14) 0.6837(3) 0.0683(6) Uani 1 1 d . . .
H13 H 0.0739 0.1997 0.6347 0.082 Uiso 1 1 calc R . .
C17 C -0.3393(4) 0.24580(14) 0.8362(3) 0.0605(6) Uani 1 1 d . . .
H17 H -0.3945 0.2838 0.8905 0.073 Uiso 1 1 calc R . .
C19 C 0.4727(3) 0.45695(12) 0.5549(2) 0.0540(5) Uani 1 1 d . . .
H19 H 0.3857 0.4981 0.5377 0.065 Uiso 1 1 calc R . .
C18 C 0.4341(3) 0.41763(11) 0.6710(2) 0.0504(5) Uani 1 1 d . . .
H18 H 0.5195 0.3758 0.6841 0.060 Uiso 1 1 calc R . .
C2 C -0.3866(4) 0.69959(16) 0.6368(3) 0.0751(7) Uani 1 1 d . . .
H2 H -0.4963 0.7099 0.5606 0.090 Uiso 1 1 calc R . .
C1 C -0.2613(4) 0.63675(14) 0.6323(3) 0.0638(6) Uani 1 1 d . . .
H1A H -0.2881 0.6045 0.5539 0.077 Uiso 1 1 calc R . .
C14 C -0.1790(5) 0.13214(16) 0.6767(4) 0.0820(8) Uani 1 1 d . . .
H14 H -0.1243 0.0936 0.6237 0.098 Uiso 1 1 calc R . .
O1 O 0.7200(4) 0.48196(13) 0.3641(2) 0.0971(7) Uani 1 1 d . . .
C15 C -0.3773(5) 0.12507(15) 0.7466(3) 0.0777(8) Uani 1 1 d . . .
H15 H -0.4580 0.0822 0.7398 0.093 Uiso 1 1 calc R . .
C22 C 0.2322(4) 0.44244(16) 1.0572(2) 0.0671(6) Uani 1 1 d . . .
H22B H 0.1647 0.4894 1.0515 0.101 Uiso 1 1 calc R . .
H22C H 0.3163 0.4369 1.1518 0.101 Uiso 1 1 calc R . .
H22A H 0.1148 0.4067 1.0475 0.101 Uiso 1 1 calc R . .
C5 C -0.0591(5) 0.67071(13) 0.8607(3) 0.0655(6) Uani 1 1 d . . .
H5 H 0.0519 0.6614 0.9368 0.079 Uiso 1 1 calc R . .
C4 C -0.1855(5) 0.73266(14) 0.8645(3) 0.0753(7) Uani 1 1 d . . .
H4 H -0.1596 0.7651 0.9425 0.090 Uiso 1 1 calc R . .
C23 C 0.5646(4) 0.48852(18) 0.9489(3) 0.0725(7) Uani 1 1 d . . .
H23A H 0.6709 0.4801 0.8740 0.109 Uiso 1 1 calc R . .
H23C H 0.6423 0.4861 1.0462 0.109 Uiso 1 1 calc R . .
H23B H 0.4980 0.5352 0.9344 0.109 Uiso 1 1 calc R . .
C3 C -0.3489(5) 0.74646(15) 0.7535(3) 0.0724(7) Uani 1 1 d . . .
H3 H -0.4356 0.7881 0.7571 0.087 Uiso 1 1 calc R . .
C21 C 0.8982(5) 0.3517(2) 0.3683(3) 0.0903(9) Uani 1 1 d . . .
H21B H 0.8558 0.3625 0.2655 0.136 Uiso 1 1 calc R . .
H21A H 0.9280 0.3013 0.3789 0.136 Uiso 1 1 calc R . .
H21C H 1.0325 0.3783 0.3997 0.136 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10 C11 C12 177.1(2) . . ?
C7 C8 C9 173.1(2) . . ?
C8 C7 C6 176.2(2) . . ?
C10 C9 N1 108.46(16) . . ?
C10 C9 C8 110.32(15) . . ?
N1 C9 C8 112.26(17) . . ?
C10 C9 C18 104.96(17) . . ?
N1 C9 C18 108.28(14) . . ?
C8 C9 C18 112.24(16) . . ?
C20 O2 C21 116.1(2) . . ?
C17 C12 C13 119.1(2) . . ?
C17 C12 C11 121.3(2) . . ?
C13 C12 C11 119.6(2) . . ?
C11 C10 C9 176.0(2) . . ?
C22 N1 C23 110.27(18) . . ?
C22 N1 C9 112.28(15) . . ?
C23 N1 C9 112.38(17) . . ?
C22 N1 H1 107.2 . . ?
C23 N1 H1 107.2 . . ?
C9 N1 H1 107.2 . . ?
O1 C20 O2 123.2(2) . . ?
O1 C20 C19 124.1(2) . . ?
O2 C20 C19 112.71(19) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 119.81(19) . . ?
C1 C6 C7 121.1(2) . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C16 C17 C12 119.6(2) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
C18 C19 C20 123.6(2) . . ?
C18 C19 H19 118.2 . . ?
C20 C19 H19 118.2 . . ?
C19 C18 C9 126.55(19) . . ?
C19 C18 H18 116.7 . . ?
C9 C18 H18 116.7 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C1 C6 119.7(2) . . ?
C2 C1 H1A 120.2 . . ?
C6 C1 H1A 120.2 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
H22B C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21A 109.5 . . ?
H21B C21 H21A 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H21A C21 H21C 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
C11 C10 1.198(3) . ?
C11 C12 1.434(3) . ?
C8 C7 1.191(3) . ?
C8 C9 1.481(3) . ?
C7 C6 1.446(3) . ?
C9 C10 1.475(3) . ?
C9 N1 1.477(2) . ?
C9 C18 1.530(3) . ?
O2 C20 1.333(3) . ?
O2 C21 1.443(3) . ?
C12 C17 1.388(3) . ?
C12 C13 1.393(4) . ?
N1 C22 1.459(3) . ?
N1 C23 1.465(3) . ?
N1 H1 0.9100 . ?
C20 O1 1.199(3) . ?
C20 C19 1.471(3) . ?
C6 C5 1.381(3) . ?
C6 C1 1.389(3) . ?
C16 C15 1.368(4) . ?
C16 C17 1.387(4) . ?
C16 H16 0.9300 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9300 . ?
C17 H17 0.9300 . ?
C19 C18 1.305(3) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C2 C3 1.370(4) . ?
C2 C1 1.386(4) . ?
C2 H2 0.9300 . ?
C1 H1A 0.9300 . ?
C14 C15 1.367(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 H22A 0.9600 . ?
C5 C4 1.375(4) . ?
C5 H5 0.9300 . ?
C4 C3 1.363(4) . ?
C4 H4 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23B 0.9600 . ?
C3 H3 0.9300 . ?
C21 H21B 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659232
