#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/29/7102997.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_7102997
loop_
_publ_author_name
'Gandon, Vincent'
'Aubert, Corinne'
'Malacria, Max'
'Vollhardt, K Peter C'
_publ_section_title
;
 Cobalt-mediated regio- and stereoselective assembly of dienamides by
 hydroaminative alkyne coupling of alpha,omega-diynes.
;
_journal_issue                   13
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1599
_journal_page_last               1601
_journal_paper_doi               10.1039/b716841a
_journal_year                    2008
_chemical_formula_moiety         'C16 H15 N O2 '
_chemical_formula_sum            'C16 H15 N O2'
_chemical_formula_weight         253.30
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             'Wed Sep 26 17:54:40 2007'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                79.270(2)
_cell_angle_beta                 81.141(2)
_cell_angle_gamma                82.075(2)
_cell_formula_units_Z            2
_cell_length_a                   7.848(1)
_cell_length_b                   8.298(1)
_cell_length_c                   10.572(2)
_cell_measurement_reflns_used    1275
_cell_measurement_temperature    177.2
_cell_measurement_theta_max      23.5
_cell_measurement_theta_min      2.5
_cell_volume                     664.1(2)
_computing_cell_refinement       'Bruker-AXS SAINT v6.40'
_computing_data_collection       'Bruker-AXS SMART v5.631'
_computing_data_reduction        'Bruker-AXS SAINT v6.40'
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_computing_structure_solution    SIR97
_diffrn_measured_fraction_theta_full 0.9853
_diffrn_measured_fraction_theta_max 0.9853
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5917
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocky
_exptl_crystal_F_000             268.00
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.651
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1727
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.0002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00022|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0521
_refine_ls_wR_factor_ref         0.0472
_reflns_number_gt                1727
_reflns_number_total             2551
_reflns_threshold_expression     F²>3.0σ(F²)
_cod_data_source_file            b716841a.txt
_cod_data_source_block           Vincent_Gandon_vgad30_at_-
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C16 H15 N O2 '
_cod_database_code               7102997
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2152(2) -0.3579(2) -0.5926(1) 0.0427(4) Uani 1.00 d . . .
O2 O -0.2275(1) 0.0321(2) -0.7154(1) 0.0455(4) Uani 1.00 d . . .
N1 N -0.0316(2) -0.1953(2) -0.6554(1) 0.0318(4) Uani 1.00 d . . .
C1 C 0.0378(3) -0.2344(3) -0.9495(2) 0.0473(6) Uani 1.00 d . . .
C2 C -0.1269(2) -0.2405(2) -0.9015(2) 0.0347(5) Uani 1.00 d . . .
C3 C -0.2748(2) -0.1581(3) -0.9740(2) 0.0440(6) Uani 1.00 d . . .
C4 C -0.3966(2) -0.2837(3) -0.9824(2) 0.0472(6) Uani 1.00 d . . .
C5 C -0.4595(2) -0.3732(3) -0.8492(2) 0.0482(7) Uani 1.00 d . . .
C6 C -0.3088(3) -0.4603(3) -0.7785(2) 0.0447(6) Uani 1.00 d . . .
C7 C -0.1826(2) -0.3403(2) -0.7738(2) 0.0341(5) Uani 1.00 d . . .
C8 C -0.1334(2) -0.3230(2) -0.6632(2) 0.0369(6) Uani 1.00 d . . .
C9 C 0.1377(2) -0.2232(2) -0.6238(2) 0.0312(5) Uani 1.00 d . . .
C10 C 0.1969(2) -0.0582(2) -0.6375(2) 0.0298(5) Uani 1.00 d . . .
C11 C 0.3563(2) -0.0139(2) -0.6261(2) 0.0371(6) Uani 1.00 d . . .
C12 C 0.3732(2) 0.1533(2) -0.6445(2) 0.0398(6) Uani 1.00 d . . .
C13 C 0.2349(2) 0.2713(2) -0.6730(2) 0.0381(6) Uani 1.00 d . . .
C14 C 0.0759(2) 0.2258(2) -0.6865(2) 0.0353(5) Uani 1.00 d . . .
C15 C 0.0606(2) 0.0599(2) -0.6698(2) 0.0291(5) Uani 1.00 d . . .
C16 C -0.0869(2) -0.0265(2) -0.6840(2) 0.0327(5) Uani 1.00 d . . .
H1 H 0.1259 -0.2954 -0.9019 0.0568 Uiso 1.00 calc . . .
H2 H 0.0685 -0.1691 -1.0316 0.0568 Uiso 1.00 calc . . .
H3 H -0.3379 -0.0741 -0.9299 0.0528 Uiso 1.00 calc . . .
H4 H -0.2298 -0.1103 -1.0593 0.0528 Uiso 1.00 calc . . .
H5 H -0.4937 -0.2276 -1.0222 0.0566 Uiso 1.00 calc . . .
H6 H -0.3362 -0.3617 -1.0335 0.0566 Uiso 1.00 calc . . .
H7 H -0.5250 -0.2957 -0.7998 0.0578 Uiso 1.00 calc . . .
H8 H -0.5312 -0.4528 -0.8580 0.0578 Uiso 1.00 calc . . .
H9 H -0.3523 -0.5064 -0.6924 0.0536 Uiso 1.00 calc . . .
H10 H -0.2503 -0.5459 -0.8228 0.0536 Uiso 1.00 calc . . .
H11 H -0.1667 -0.3977 -0.5865 0.0443 Uiso 1.00 calc . . .
H12 H 0.4508 -0.0948 -0.6063 0.0446 Uiso 1.00 calc . . .
H13 H 0.4814 0.1877 -0.6375 0.0477 Uiso 1.00 calc . . .
H14 H 0.2494 0.3850 -0.6835 0.0457 Uiso 1.00 calc . . .
H15 H -0.0189 0.3062 -0.7065 0.0424 Uiso 1.00 calc . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C9 124.4(1) . . . ?
C8 N1 C16 124.1(1) . . . ?
C9 N1 C16 111.5(1) . . . ?
C1 C2 C3 123.6(2) . . . ?
C1 C2 C7 122.4(2) . . . ?
C3 C2 C7 113.9(1) . . . ?
C2 C3 C4 110.5(2) . . . ?
C3 C4 C5 111.1(2) . . . ?
C4 C5 C6 111.5(2) . . . ?
C5 C6 C7 110.6(2) . . . ?
C2 C7 C6 114.2(1) . . . ?
C2 C7 C8 123.9(2) . . . ?
C6 C7 C8 121.8(2) . . . ?
N1 C8 C7 122.1(2) . . . ?
O1 C9 N1 124.9(2) . . . ?
O1 C9 C10 129.0(2) . . . ?
N1 C9 C10 106.1(1) . . . ?
C9 C10 C11 130.6(2) . . . ?
C9 C10 C15 108.2(1) . . . ?
C11 C10 C15 121.2(2) . . . ?
C10 C11 C12 117.4(2) . . . ?
C11 C12 C13 121.2(2) . . . ?
C12 C13 C14 121.0(2) . . . ?
C13 C14 C15 117.5(2) . . . ?
C10 C15 C14 121.6(2) . . . ?
C10 C15 C16 108.1(2) . . . ?
C14 C15 C16 130.3(2) . . . ?
O2 C16 N1 125.2(2) . . . ?
O2 C16 C15 128.7(2) . . . ?
N1 C16 C15 106.0(1) . . . ?
C2 C1 H1 120.000 . . . no
C2 C1 H2 120.000 . . . no
H1 C1 H2 120.000 . . . no
C2 C3 H3 109.208 . . . no
C2 C3 H4 109.207 . . . no
C4 C3 H3 109.207 . . . no
C4 C3 H4 109.207 . . . no
H3 C3 H4 109.460 . . . no
C3 C4 H5 109.077 . . . no
C3 C4 H6 109.077 . . . no
C5 C4 H5 109.077 . . . no
C5 C4 H6 109.077 . . . no
H5 C4 H6 109.460 . . . no
C4 C5 H7 108.971 . . . no
C4 C5 H8 108.971 . . . no
C6 C5 H7 108.970 . . . no
C6 C5 H8 108.971 . . . no
H7 C5 H8 109.460 . . . no
C5 C6 H9 109.194 . . . no
C5 C6 H10 109.194 . . . no
C7 C6 H9 109.195 . . . no
C7 C6 H10 109.195 . . . no
H9 C6 H10 109.460 . . . no
N1 C8 H11 118.925 . . . no
C7 C8 H11 118.925 . . . no
C10 C11 H12 121.288 . . . no
C12 C11 H12 121.288 . . . no
C11 C12 H13 119.388 . . . no
C13 C12 H13 119.388 . . . no
C12 C13 H14 119.483 . . . no
C14 C13 H14 119.484 . . . no
C13 C14 H15 121.258 . . . no
C15 C14 H15 121.259 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.210(2) . . yes
O2 C16 1.212(2) . . yes
N1 C8 1.433(2) . . yes
N1 C9 1.398(2) . . yes
N1 C16 1.399(2) . . yes
C1 C2 1.318(3) . . yes
C2 C3 1.505(3) . . yes
C2 C7 1.484(3) . . yes
C3 C4 1.530(3) . . yes
C4 C5 1.509(3) . . yes
C5 C6 1.522(3) . . yes
C6 C7 1.510(3) . . yes
C7 C8 1.324(2) . . yes
C9 C10 1.480(3) . . yes
C10 C11 1.380(2) . . yes
C10 C15 1.386(2) . . yes
C11 C12 1.386(3) . . yes
C12 C13 1.387(2) . . yes
C13 C14 1.388(2) . . yes
C14 C15 1.374(3) . . yes
C15 C16 1.482(2) . . yes
C1 H1 0.950 . . no
C1 H2 0.950 . . no
C3 H3 0.950 . . no
C3 H4 0.950 . . no
C4 H5 0.950 . . no
C4 H6 0.950 . . no
C5 H7 0.950 . . no
C5 H8 0.950 . . no
C6 H9 0.950 . . no
C6 H10 0.950 . . no
C8 H11 0.950 . . no
C11 H12 0.950 . . no
C12 H13 0.950 . . no
C13 H14 0.950 . . no
C14 H15 0.950 . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C13 3.319(2) . 1_545 ?
O1 C5 3.435(2) . 1_655 ?
O1 C8 3.465(2) . 2_544 ?
O2 C12 3.175(2) . 1_455 ?
O2 C11 3.312(2) . 1_455 ?
O2 C11 3.577(2) . 2_554 ?
N1 C14 3.543(2) . 2_554 ?
N1 C13 3.572(2) . 2_554 ?
C9 C14 3.444(3) . 2_554 ?
C10 C15 3.551(3) . 2_554 ?
C10 C16 3.551(2) . 2_554 ?
C15 C15 3.558(3) . 2_554 ?
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 C9 N1 C8 -4.1(3) 1_555 1_555 1_555 1_555 yes
O1 C9 N1 C16 178.4(2) 1_555 1_555 1_555 1_555 yes
O1 C9 C10 C11 4.2(3) 1_555 1_555 1_555 1_555 yes
O1 C9 C10 C15 -177.4(2) 1_555 1_555 1_555 1_555 yes
O2 C16 N1 C8 1.8(3) 1_555 1_555 1_555 1_555 yes
O2 C16 N1 C9 179.3(2) 1_555 1_555 1_555 1_555 yes
O2 C16 C15 C10 -177.4(2) 1_555 1_555 1_555 1_555 yes
O2 C16 C15 C14 1.0(3) 1_555 1_555 1_555 1_555 yes
N1 C8 C7 C2 5.2(3) 1_555 1_555 1_555 1_555 yes
N1 C8 C7 C6 -171.9(2) 1_555 1_555 1_555 1_555 yes
N1 C9 C10 C11 -175.5(2) 1_555 1_555 1_555 1_555 yes
N1 C9 C10 C15 2.9(2) 1_555 1_555 1_555 1_555 yes
N1 C16 C15 C10 1.6(2) 1_555 1_555 1_555 1_555 yes
N1 C16 C15 C14 180.0(2) 1_555 1_555 1_555 1_555 yes
C1 C2 C3 C4 124.4(2) 1_555 1_555 1_555 1_555 yes
C1 C2 C7 C6 -125.6(2) 1_555 1_555 1_555 1_555 yes
C1 C2 C7 C8 57.2(3) 1_555 1_555 1_555 1_555 yes
C2 C3 C4 C5 55.0(2) 1_555 1_555 1_555 1_555 yes
C2 C7 C6 C5 -50.6(2) 1_555 1_555 1_555 1_555 yes
C3 C2 C7 C6 50.3(2) 1_555 1_555 1_555 1_555 yes
C3 C2 C7 C8 -127.0(2) 1_555 1_555 1_555 1_555 yes
C3 C4 C5 C6 -57.6(2) 1_555 1_555 1_555 1_555 yes
C4 C3 C2 C7 -51.4(2) 1_555 1_555 1_555 1_555 yes
C4 C5 C6 C7 54.4(2) 1_555 1_555 1_555 1_555 yes
C5 C6 C7 C8 126.7(2) 1_555 1_555 1_555 1_555 yes
C7 C8 N1 C9 -114.9(2) 1_555 1_555 1_555 1_555 yes
C7 C8 N1 C16 62.3(2) 1_555 1_555 1_555 1_555 yes
C8 N1 C9 C10 175.6(2) 1_555 1_555 1_555 1_555 yes
C8 N1 C16 C15 -177.2(2) 1_555 1_555 1_555 1_555 yes
C9 N1 C16 C15 0.3(2) 1_555 1_555 1_555 1_555 yes
C9 C10 C11 C12 180.0(2) 1_555 1_555 1_555 1_555 yes
C9 C10 C15 C14 178.7(2) 1_555 1_555 1_555 1_555 yes
C9 C10 C15 C16 -2.8(2) 1_555 1_555 1_555 1_555 yes
C10 C9 N1 C16 -1.9(2) 1_555 1_555 1_555 1_555 yes
C10 C11 C12 C13 0.2(3) 1_555 1_555 1_555 1_555 yes
C10 C15 C14 C13 1.6(3) 1_555 1_555 1_555 1_555 yes
C11 C10 C15 C14 -2.7(3) 1_555 1_555 1_555 1_555 yes
C11 C10 C15 C16 175.8(2) 1_555 1_555 1_555 1_555 yes
C11 C12 C13 C14 -1.2(3) 1_555 1_555 1_555 1_555 yes
C12 C11 C10 C15 1.8(3) 1_555 1_555 1_555 1_555 yes
C12 C13 C14 C15 0.4(3) 1_555 1_555 1_555 1_555 yes
C13 C14 C15 C16 -176.6(2) 1_555 1_555 1_555 1_555 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21195011
