#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/78/1517866.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_1517866
loop_
_publ_author_name
'Gobé, Valérian'
'Retailleau, Pascal'
'Guinchard, Xavier'
_publ_section_title
;
 Domino Formation of Enamines - Intramolecular Cyclizations to
 1-Aminotetralins from γ-Arylallene Aldehydes and Amines.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5438
_journal_page_last               5441
_journal_paper_doi               10.1021/ol5026712
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C18 H23 N O'
_chemical_formula_sum            'C18 H23 N O'
_chemical_formula_weight         269.37
_chemical_name_systematic
;
 4-(1,2,3,8a,9,9a,10,10a-octahydroanthracen-9-yl)morpholine
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 95.087(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.618(1)
_cell_length_b                   16.963(1)
_cell_length_c                   10.051(1)
_cell_measurement_reflns_used    2990
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.103
_cell_measurement_theta_min      0.998
_cell_volume                     1463.5(2)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14179
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         27.098
_diffrn_reflns_theta_min         2.362
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       stick
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0486
_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)+(0.0670P)²+0.1504P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2004
_reflns_number_total             3197
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5026712_si_002.cif
_cod_data_source_block           vg620
_cod_depositor_comments          'Adding full bibliography for 1517866.cif.'
_cod_database_code               1517866
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
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 0.80598(17) 0.03111(6) 0.69380(13) 0.0807(4) Uani 1 1 d . . . . .
C1 C 0.57357(18) 0.24468(7) 0.57753(14) 0.0459(4) Uani 1 1 d . . . . .
H1 H 0.5629 0.2458 0.4797 0.055 Uiso 1 1 calc R U . . .
N2 N 0.67403(15) 0.17761(6) 0.61521(11) 0.0484(3) Uani 1 1 d . . . . .
C2 C 0.40514(18) 0.24261(8) 0.62123(17) 0.0554(4) Uani 1 1 d . U . . .
H2 H 0.4165 0.2500 0.7183 0.067 Uiso 0.679(8) 1 calc R U P A 1
H2B H 0.4016 0.2368 0.7179 0.067 Uiso 0.321(8) 1 calc R U P A 2
C3 C 0.32307(18) 0.31567(9) 0.56573(15) 0.0545(4) Uani 1 1 d . . . . .
C6 C 0.65386(17) 0.32214(8) 0.62230(13) 0.0450(4) Uani 1 1 d . . . . .
C5 C 0.56735(18) 0.39084(8) 0.63870(13) 0.0482(4) Uani 1 1 d . . . . .
C4 C 0.39171(19) 0.39159(9) 0.61889(17) 0.0591(4) Uani 1 1 d . . . . .
H4A H 0.3509 0.4030 0.7037 0.071 Uiso 1 1 calc R U . . .
H4B H 0.3588 0.4337 0.5575 0.071 Uiso 1 1 calc R U . . .
C9 C 0.1284(2) 0.23897(10) 0.4191(2) 0.0716(5) Uani 1 1 d . U . . .
H9A H 0.1083 0.2435 0.3229 0.086 Uiso 0.679(8) 1 calc R U P A 1
H9B H 0.0298 0.2306 0.4566 0.086 Uiso 0.679(8) 1 calc R U P A 1
H9C H 0.1676 0.2271 0.3338 0.086 Uiso 0.321(8) 1 calc R U P A 2
H9D H 0.0167 0.2466 0.4042 0.086 Uiso 0.321(8) 1 calc R U P A 2
C10 C 0.20254(19) 0.31278(10) 0.47446(17) 0.0636(5) Uani 1 1 d . U . . .
H10 H 0.1610 0.3604 0.4425 0.076 Uiso 1 1 calc R U . . .
C12 C 0.8905(2) 0.39576(10) 0.68052(17) 0.0660(5) Uani 1 1 d . . . . .
H12 H 0.9986 0.3971 0.6944 0.079 Uiso 1 1 calc R U . . .
C11 C 0.81522(19) 0.32646(9) 0.64362(15) 0.0566(4) Uani 1 1 d . . . . .
H11 H 0.8740 0.2813 0.6327 0.068 Uiso 1 1 calc R U . . .
C15 C 0.68097(19) 0.15247(9) 0.75339(14) 0.0539(4) Uani 1 1 d . . . . .
H15A H 0.5835 0.1274 0.7705 0.065 Uiso 1 1 calc R U . . .
H15B H 0.6958 0.1980 0.8116 0.065 Uiso 1 1 calc R U . . .
C14 C 0.6458(2) 0.46010(9) 0.67559(15) 0.0599(4) Uani 1 1 d . . . . .
H14 H 0.5886 0.5058 0.6862 0.072 Uiso 1 1 calc R U . . .
C13 C 0.8050(2) 0.46307(10) 0.69675(17) 0.0673(5) Uani 1 1 d . . . . .
H13 H 0.8548 0.5101 0.7218 0.081 Uiso 1 1 calc R U . . .
C16 C 0.8129(2) 0.09560(10) 0.78269(18) 0.0699(5) Uani 1 1 d . . . . .
H16A H 0.9108 0.1232 0.7773 0.084 Uiso 1 1 calc R U . . .
H16B H 0.8108 0.0761 0.8732 0.084 Uiso 1 1 calc R U . . .
C17 C 0.8059(3) 0.05873(11) 0.56034(19) 0.0846(6) Uani 1 1 d . . . . .
H17A H 0.8019 0.0140 0.4999 0.102 Uiso 1 1 calc R U . . .
H17B H 0.9019 0.0871 0.5506 0.102 Uiso 1 1 calc R U . . .
C18 C 0.6708(2) 0.11160(9) 0.52323(16) 0.0707(5) Uani 1 1 d . . . . .
H18A H 0.6758 0.1308 0.4328 0.085 Uiso 1 1 calc R U . . .
H18B H 0.5743 0.0825 0.5266 0.085 Uiso 1 1 calc R U . . .
C7 C 0.3026(4) 0.1706(2) 0.5977(5) 0.0574(9) Uani 0.679(8) 1 d . U P A 1
H7A H 0.3632 0.1232 0.6181 0.069 Uiso 0.679(8) 1 calc R U P A 1
H7B H 0.2185 0.1722 0.6557 0.069 Uiso 0.679(8) 1 calc R U P A 1
C8 C 0.2367(5) 0.16921(16) 0.4534(4) 0.0658(10) Uani 0.679(8) 1 d . U P A 1
H8A H 0.1795 0.1205 0.4359 0.079 Uiso 0.679(8) 1 calc R U P A 1
H8B H 0.3217 0.1704 0.3962 0.079 Uiso 0.679(8) 1 calc R U P A 1
C7B C 0.3384(9) 0.1640(4) 0.5353(10) 0.0535(18) Uani 0.321(8) 1 d . U P A 2
H7BA H 0.3825 0.1620 0.4499 0.064 Uiso 0.321(8) 1 calc R U P A 2
H7BB H 0.3678 0.1163 0.5844 0.064 Uiso 0.321(8) 1 calc R U P A 2
C8B C 0.1625(9) 0.1702(4) 0.5139(10) 0.070(2) Uani 0.321(8) 1 d . U P A 2
H8BA H 0.1186 0.1797 0.5980 0.084 Uiso 0.321(8) 1 calc R U P A 2
H8BB H 0.1183 0.1219 0.4753 0.084 Uiso 0.321(8) 1 calc R U P A 2
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
C16 O1 C17 109.80(13)
N2 C1 C6 110.48(12)
N2 C1 C2 117.17(11)
C6 C1 C2 110.17(11)
C15 N2 C18 112.36(12)
C15 N2 C1 116.83(11)
C18 N2 C1 117.32(12)
C3 C2 C7 110.92(17)
C3 C2 C1 107.21(12)
C7 C2 C1 121.4(2)
C3 C2 C7B 109.7(3)
C1 C2 C7B 99.2(4)
C10 C3 C4 122.71(14)
C10 C3 C2 122.60(15)
C4 C3 C2 114.67(13)
C11 C6 C5 118.26(13)
C11 C6 C1 120.63(13)
C5 C6 C1 121.08(13)
C14 C5 C6 118.91(14)
C14 C5 C4 119.12(14)
C6 C5 C4 121.97(13)
C3 C4 C5 113.58(13)
C10 C9 C8B 111.0(3)
C10 C9 C8 109.49(17)
C3 C10 C9 124.99(15)
C13 C12 C11 119.69(16)
C12 C11 C6 121.83(15)
N2 C15 C16 110.09(13)
C13 C14 C5 121.95(15)
C14 C13 C12 119.36(15)
O1 C16 C15 112.68(14)
O1 C17 C18 111.69(15)
N2 C18 C17 109.55(15)
C8 C7 C2 109.1(3)
C7 C8 C9 112.0(3)
C8B C7B C2 108.3(7)
C7B C8B C9 106.1(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C16 1.410(2)
O1 C17 1.421(2)
C1 N2 1.4592(17)
C1 C6 1.5337(18)
C1 C2 1.554(2)
N2 C15 1.4490(18)
N2 C18 1.4508(19)
C2 C3 1.509(2)
C2 C7 1.514(3)
C2 C7B 1.663(7)
C3 C10 1.324(2)
C3 C4 1.496(2)
C6 C11 1.390(2)
C6 C5 1.4010(19)
C5 C14 1.389(2)
C5 C4 1.509(2)
C9 C10 1.491(2)
C9 C8B 1.519(7)
C9 C8 1.527(4)
C12 C13 1.376(2)
C12 C11 1.378(2)
C15 C16 1.500(2)
C14 C13 1.371(2)
C17 C18 1.491(3)
C7 C8 1.511(6)
C7B C8B 1.516(13)
