#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/06/7110602.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7110602
loop_
_publ_author_name
'Ventrice, Tina'
'Campi, Eva M.'
'Roy Jackson, W.'
'Patti, Antonio F.'
_publ_section_title
;
 A new route to medium and large heterocyclic compounds
;
_journal_issue                   16
_journal_name_full               'Chemical Communications'
_journal_page_first              1463
_journal_paper_doi               10.1039/a904168k
_journal_year                    1999
_chemical_formula_moiety         'C25 H33 N O2 '
_chemical_formula_sum            'C25 H33 N O2'
_chemical_formula_weight         379.54
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             1998-08-01
_audit_creation_method           'by teXsan v1.8'
_cell_angle_alpha                90
_cell_angle_beta                 99.648(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3905(1)
_cell_length_b                   23.1162(5)
_cell_length_c                   10.0908(2)
_cell_measurement_temperature    123(2)
_cell_volume                     2159.46(7)
_diffrn_ambient_temperature      123(2)
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15214
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.792
_refine_ls_goodness_of_fit_ref   2.021
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     352
_refine_ls_number_reflns         3258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo)]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0421
_refine_ls_wR_factor_ref         0.0388
_reflns_number_gt                3258
_reflns_number_total             4843
_reflns_threshold_expression     I>3.00σ(I)
_cod_data_source_file            904168ksup1.cif
_cod_data_source_block           5n
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2159.46(6)
_cod_original_sg_symbol_H-M      'P 21/n     '
_cod_original_formula_sum        'C25 H33 N O2 '
_cod_database_code               7110602
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
1/2-x,1/2+y,1/2-z
'   -x,   -y,   -z'
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_calc_flag
O(1) 0.97771(8) 0.16919(4) 0.84110(9) 0.0297(3) 1.000 Uani d
O(28) 1.31872(8) 0.15241(4) 0.6989(1) 0.0354(3) 1.000 Uani d
N(14) 1.0956(1) 0.11386(5) 0.6481(1) 0.0254(3) 1.000 Uani d
C(2) 0.9283(1) 0.20687(7) 0.9373(1) 0.0339(4) 1.000 Uani d
C(3) 1.0479(2) 0.21082(6) 1.0564(2) 0.0353(4) 1.000 Uani d
C(4) 1.0737(1) 0.15418(6) 1.1335(2) 0.0326(4) 1.000 Uani d
C(5) 1.2108(1) 0.15405(7) 1.2380(2) 0.0361(4) 1.000 Uani d
C(6) 1.2283(2) 0.10052(7) 1.3276(2) 0.0416(5) 1.000 Uani d
C(7) 1.2243(2) 0.04273(7) 1.2535(2) 0.0393(4) 1.000 Uani d
C(8) 1.3426(1) 0.03580(7) 1.1678(2) 0.0340(4) 1.000 Uani d
C(9) 1.3485(1) -0.02403(6) 1.1068(2) 0.0356(4) 1.000 Uani d
C(10) 1.2201(1) -0.04260(7) 1.0013(1) 0.0326(4) 1.000 Uani d
C(11) 1.2182(1) -0.02102(6) 0.8582(1) 0.0312(4) 1.000 Uani d
C(12) 1.1731(1) 0.04147(6) 0.8294(1) 0.0295(4) 1.000 Uani d
C(13) 1.1541(1) 0.05574(6) 0.6807(1) 0.0299(4) 1.000 Uani d
C(14a) 0.9416(1) 0.12126(6) 0.6344(1) 0.0258(3) 1.000 Uani d
C(15) 0.8524(1) 0.09739(6) 0.5251(1) 0.0309(4) 1.000 Uani d
C(16) 0.7037(1) 0.10338(6) 0.5107(2) 0.0360(4) 1.000 Uani d
C(17) 0.6450(1) 0.13482(6) 0.6051(2) 0.0359(4) 1.000 Uani d
C(18) 0.7334(1) 0.15869(6) 0.7153(2) 0.0326(4) 1.000 Uani d
C(18a) 0.8823(1) 0.15067(6) 0.7328(1) 0.0260(4) 1.000 Uani d
C(19) 1.1885(1) 0.15943(6) 0.6611(1) 0.0260(3) 1.000 Uani d
C(20) 1.1304(1) 0.21832(5) 0.6219(1) 0.0251(3) 1.000 Uani d
C(21) 1.0440(1) 0.22900(6) 0.4984(1) 0.0298(4) 1.000 Uani d
C(22) 1.0042(1) 0.28498(6) 0.4604(2) 0.0347(4) 1.000 Uani d
C(23) 1.0471(1) 0.33043(7) 0.5463(2) 0.0379(4) 1.000 Uani d
C(24) 1.1312(1) 0.32029(7) 0.6699(2) 0.0383(4) 1.000 Uani d
C(25) 1.1739(1) 0.26460(6) 0.7071(2) 0.0316(4) 1.000 Uani d
H(1) 0.908(1) 0.2454(7) 0.891(2) 0.044 1.000 Uiso d
H(2) 0.840(2) 0.1895(6) 0.964(1) 0.044 1.000 Uiso d
H(3) 1.024(1) 0.2414(7) 1.115(2) 0.044 1.000 Uiso d
H(4) 1.137(2) 0.2223(6) 1.026(2) 0.044 1.000 Uiso d
H(5) 0.990(2) 0.1457(6) 1.181(1) 0.044 1.000 Uiso d
H(6) 1.076(1) 0.1225(7) 1.069(1) 0.044 1.000 Uiso d
H(7) 1.209(1) 0.1898(7) 1.297(2) 0.044 1.000 Uiso d
H(8) 1.298(2) 0.1568(6) 1.189(2) 0.044 1.000 Uiso d
H(9) 1.152(2) 0.1012(6) 1.388(2) 0.044 1.000 Uiso d
H(10) 1.325(2) 0.1041(6) 1.395(2) 0.044 1.000 Uiso d
H(11) 1.235(1) 0.0104(7) 1.322(2) 0.044 1.000 Uiso d
H(12) 1.125(2) 0.0366(6) 1.195(2) 0.044 1.000 Uiso d
H(13) 1.442(2) 0.0445(6) 1.229(2) 0.044 1.000 Uiso d
H(14) 1.334(1) 0.0661(7) 1.096(2) 0.044 1.000 Uiso d
H(15) 1.361(1) -0.0526(7) 1.182(2) 0.044 1.000 Uiso d
H(16) 1.436(2) -0.0271(6) 1.065(1) 0.044 1.000 Uiso d
H(17) 1.222(1) -0.0848(7) 1.000(1) 0.044 1.000 Uiso d
H(18) 1.128(2) -0.0314(6) 1.034(1) 0.044 1.000 Uiso d
H(19) 1.314(2) -0.0269(6) 0.833(1) 0.044 1.000 Uiso d
H(20) 1.151(1) -0.0462(7) 0.796(2) 0.044 1.000 Uiso d
H(21) 1.247(1) 0.0690(7) 0.878(2) 0.044 1.000 Uiso d
H(22) 1.078(2) 0.0493(6) 0.862(2) 0.044 1.000 Uiso d
H(23) 1.250(1) 0.0528(6) 0.650(1) 0.044 1.000 Uiso d
H(24) 1.087(1) 0.0272(6) 0.626(2) 0.044 1.000 Uiso d
H(25) 0.895(1) 0.0768(7) 0.458(2) 0.044 1.000 Uiso d
H(26) 0.643(2) 0.0864(6) 0.433(2) 0.044 1.000 Uiso d
H(27) 0.538(2) 0.1400(6) 0.591(1) 0.044 1.000 Uiso d
H(28) 0.690(1) 0.1819(7) 0.785(2) 0.044 1.000 Uiso d
H(29) 1.015(1) 0.1967(7) 0.437(2) 0.044 1.000 Uiso d
H(30) 0.948(1) 0.2926(7) 0.374(2) 0.044 1.000 Uiso d
H(31) 1.019(1) 0.3688(7) 0.519(2) 0.044 1.000 Uiso d
H(32) 1.160(1) 0.3513(7) 0.727(2) 0.044 1.000 Uiso d
H(33) 1.235(1) 0.2571(7) 0.794(2) 0.044 1.000 Uiso d
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 100 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 132 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0 4 0.004 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O 0 8 0.008 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(2) O(1) C(18a) 119.27(9) yes
C(13) N(14) C(14a) 117.5(1) yes
C(13) N(14) C(19) 118.5(1) yes
C(14a) N(14) C(19) 122.3(1) yes
O(1) C(2) C(3) 107.1(1) yes
O(1) C(2) H(1) 106.5(9) no
O(1) C(2) H(2) 108.3(9) no
C(3) C(2) H(1) 111.8(8) no
C(3) C(2) H(2) 110.6(8) no
H(1) C(2) H(2) 112(1) no
C(2) C(3) C(4) 112.9(1) yes
C(2) C(3) H(3) 108.2(8) no
C(2) C(3) H(4) 109.2(9) no
C(4) C(3) H(3) 110.5(9) no
C(4) C(3) H(4) 108.9(9) no
H(3) C(3) H(4) 107(1) no
C(3) C(4) C(5) 113.6(1) yes
C(3) C(4) H(5) 110.0(8) no
C(3) C(4) H(6) 108.6(9) no
C(5) C(4) H(5) 107.9(8) no
C(5) C(4) H(6) 110.3(8) no
H(5) C(4) H(6) 106(1) no
C(4) C(5) C(6) 114.0(1) yes
C(4) C(5) H(7) 108.1(8) no
C(4) C(5) H(8) 108.4(8) no
C(6) C(5) H(7) 108.8(9) no
C(6) C(5) H(8) 108.8(8) no
H(7) C(5) H(8) 109(1) no
C(5) C(6) C(7) 115.3(1) yes
C(5) C(6) H(9) 109.0(8) no
C(5) C(6) H(10) 108.6(8) no
C(7) C(6) H(9) 110.1(8) no
C(7) C(6) H(10) 109.6(8) no
H(9) C(6) H(10) 104(1) no
C(6) C(7) C(8) 114.1(1) yes
C(6) C(7) H(11) 108.6(9) no
C(6) C(7) H(12) 110.4(8) no
C(8) C(7) H(11) 108.2(8) no
C(8) C(7) H(12) 109.4(9) no
H(11) C(7) H(12) 106(1) no
C(7) C(8) C(9) 113.9(1) yes
C(7) C(8) H(13) 107.8(8) no
C(7) C(8) H(14) 111.2(8) no
C(9) C(8) H(13) 108.9(8) no
C(9) C(8) H(14) 110.3(9) no
H(13) C(8) H(14) 104(1) no
C(8) C(9) C(10) 117.3(1) yes
C(8) C(9) H(15) 107.8(9) no
C(8) C(9) H(16) 109.2(8) no
C(10) C(9) H(15) 108.6(8) no
C(10) C(9) H(16) 107.3(8) no
H(15) C(9) H(16) 106(1) no
C(9) C(10) C(11) 116.7(1) yes
C(9) C(10) H(17) 106.1(8) no
C(9) C(10) H(18) 108.8(8) no
C(11) C(10) H(17) 107.9(9) no
C(11) C(10) H(18) 110.4(8) no
H(17) C(10) H(18) 106(1) no
C(10) C(11) C(12) 116.8(1) yes
C(10) C(11) H(19) 109.6(8) no
C(10) C(11) H(20) 108.2(9) no
C(12) C(11) H(19) 108.6(8) no
C(12) C(11) H(20) 107.7(8) no
H(19) C(11) H(20) 105(1) no
C(11) C(12) C(13) 112.3(1) yes
C(11) C(12) H(21) 111.1(8) no
C(11) C(12) H(22) 109.7(8) no
C(13) C(12) H(21) 107.6(9) no
C(13) C(12) H(22) 108.5(8) no
H(21) C(12) H(22) 107(1) no
N(14) C(13) C(12) 113.5(1) yes
N(14) C(13) H(23) 108.2(8) no
N(14) C(13) H(24) 107.3(8) no
C(12) C(13) H(23) 109.4(8) no
C(12) C(13) H(24) 111.2(9) no
H(23) C(13) H(24) 107(1) no
N(14) C(14a) C(15) 119.6(1) yes
N(14) C(14a) C(18a) 120.3(1) yes
C(15) C(14a) C(18a) 120.1(1) yes
C(14a) C(15) C(16) 120.6(1) yes
C(14a) C(15) H(25) 119.1(8) no
C(16) C(15) H(25) 120.3(8) no
C(15) C(16) C(17) 119.3(1) yes
C(15) C(16) H(26) 119.3(9) no
C(17) C(16) H(26) 121.3(8) no
C(16) C(17) C(18) 120.5(1) yes
C(16) C(17) H(27) 118.3(9) no
C(18) C(17) H(27) 121.2(9) no
C(17) C(18) C(18a) 120.2(1) yes
C(17) C(18) H(28) 120.5(8) no
C(18a) C(18) H(28) 119.3(8) no
O(1) C(18a) C(14a) 115.9(1) yes
O(1) C(18a) C(18) 124.9(1) yes
C(14a) C(18a) C(18) 119.2(1) yes
O(28) C(19) N(14) 121.1(1) yes
O(28) C(19) C(20) 120.2(1) yes
N(14) C(19) C(20) 118.7(1) yes
C(19) C(20) C(21) 122.1(1) yes
C(19) C(20) C(25) 118.7(1) yes
C(21) C(20) C(25) 119.0(1) yes
C(20) C(21) C(22) 120.3(1) yes
C(20) C(21) H(29) 119.5(9) no
C(22) C(21) H(29) 120.1(9) no
C(21) C(22) C(23) 120.1(1) yes
C(21) C(22) H(30) 120.4(9) no
C(23) C(22) H(30) 119.5(9) no
C(22) C(23) C(24) 120.1(1) yes
C(22) C(23) H(31) 119.5(9) no
C(24) C(23) H(31) 120.4(9) no
C(23) C(24) C(25) 120.0(1) yes
C(23) C(24) H(32) 119.6(9) no
C(25) C(24) H(32) 120.4(9) no
C(20) C(25) C(24) 120.5(1) yes
C(20) C(25) H(33) 118.9(9) no
C(24) C(25) H(33) 120.6(9) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(2) 1.438(2) yes
O(1) C(18a) 1.361(2) yes
O(28) C(19) 1.229(1) yes
N(14) C(13) 1.468(2) yes
N(14) C(14a) 1.440(1) yes
N(14) C(19) 1.360(2) yes
C(2) C(3) 1.504(2) yes
C(2) H(1) 1.01(2) no
C(2) H(2) 1.00(2) no
C(3) C(4) 1.521(2) yes
C(3) H(3) 0.97(2) no
C(3) H(4) 0.98(1) no
C(4) C(5) 1.521(2) yes
C(4) H(5) 1.00(2) no
C(4) H(6) 0.98(2) no
C(5) C(6) 1.525(2) yes
C(5) H(7) 1.02(2) no
C(5) H(8) 1.03(1) no
C(6) C(7) 1.528(2) yes
C(6) H(9) 1.02(2) no
C(6) H(10) 1.04(1) no
C(7) C(8) 1.526(2) yes
C(7) H(11) 1.01(2) no
C(7) H(12) 1.02(1) no
C(8) C(9) 1.518(2) yes
C(8) H(13) 1.05(1) no
C(8) H(14) 1.00(2) no
C(9) C(10) 1.530(2) yes
C(9) H(15) 1.00(2) no
C(9) H(16) 0.99(1) no
C(10) C(11) 1.525(2) yes
C(10) H(17) 0.98(2) no
C(10) H(18) 1.01(2) no
C(11) C(12) 1.520(2) yes
C(11) H(19) 0.99(1) no
C(11) H(20) 1.00(1) no
C(12) C(13) 1.517(2) yes
C(12) H(21) 1.01(1) no
C(12) H(22) 1.02(1) no
C(13) H(23) 1.00(1) no
C(13) H(24) 1.01(1) no
C(14a) C(15) 1.383(2) yes
C(14a) C(18a) 1.395(2) yes
C(15) C(16) 1.387(2) yes
C(15) H(25) 0.97(2) no
C(16) C(17) 1.384(2) yes
C(16) H(26) 0.97(1) no
C(17) C(18) 1.386(2) yes
C(17) H(27) 1.00(1) no
C(18) C(18a) 1.392(2) yes
C(18) H(28) 1.02(2) no
C(19) C(20) 1.495(2) yes
C(20) C(21) 1.390(2) yes
C(20) C(25) 1.390(2) yes
C(21) C(22) 1.383(2) yes
C(21) H(29) 0.98(2) no
C(22) C(23) 1.379(2) yes
C(22) H(30) 0.96(2) no
C(23) C(24) 1.379(2) yes
C(23) H(31) 0.95(2) no
C(24) C(25) 1.382(2) yes
C(24) H(32) 0.93(2) no
C(25) H(33) 0.98(1) no
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_publ_flag
O(1) C(2) C(3) C(4) -67.8(2) no
O(1) C(18a) C(14a) N(14) -2.3(2) no
O(1) C(18a) C(14a) C(15) 175.6(1) no
O(1) C(18a) C(18) C(17) -175.8(1) no
O(28) C(19) N(14) C(13) 0.3(2) no
O(28) C(19) N(14) C(14a) 165.4(1) no
O(28) C(19) C(20) C(21) 126.5(1) no
O(28) C(19) C(20) C(25) -48.1(2) no
N(14) C(13) C(12) C(11) 173.8(1) no
N(14) C(14a) C(15) C(16) 179.2(1) no
N(14) C(14a) C(18a) C(18) 178.2(1) no
N(14) C(19) C(20) C(21) -50.5(2) no
N(14) C(19) C(20) C(25) 134.9(1) no
C(2) O(1) C(18a) C(14a) 171.1(1) no
C(2) O(1) C(18a) C(18) -9.4(2) no
C(2) C(3) C(4) C(5) 169.4(1) no
C(3) C(2) O(1) C(18a) 169.6(1) no
C(3) C(4) C(5) C(6) 172.8(1) no
C(4) C(5) C(6) C(7) 56.2(2) no
C(5) C(6) C(7) C(8) 60.2(2) no
C(6) C(7) C(8) C(9) 173.6(1) no
C(7) C(8) C(9) C(10) 66.4(2) no
C(8) C(9) C(10) C(11) 81.6(2) no
C(9) C(10) C(11) C(12) -77.4(2) no
C(10) C(11) C(12) C(13) -171.7(1) no
C(12) C(13) N(14) C(14a) -82.0(1) no
C(12) C(13) N(14) C(19) 83.9(1) no
C(13) N(14) C(14a) C(15) -70.3(2) no
C(13) N(14) C(14a) C(18a) 107.6(1) no
C(13) N(14) C(19) C(20) 177.2(1) no
C(14a) N(14) C(19) C(20) -17.6(2) no
C(14a) C(15) C(16) C(17) 1.6(2) no
C(14a) C(18a) C(18) C(17) 3.7(2) no
C(15) C(14a) N(14) C(19) 124.4(1) no
C(15) C(14a) C(18a) C(18) -3.9(2) no
C(15) C(16) C(17) C(18) -1.9(2) no
C(16) C(15) C(14a) C(18a) 1.3(2) no
C(16) C(17) C(18) C(18a) -0.8(2) no
C(18a) C(14a) N(14) C(19) -57.7(2) no
C(19) C(20) C(21) C(22) -173.5(1) no
C(19) C(20) C(25) C(24) 175.2(1) no
C(20) C(21) C(22) C(23) -1.7(2) no
C(20) C(25) C(24) C(23) -1.3(2) no
C(21) C(20) C(25) C(24) 0.4(2) no
C(21) C(22) C(23) C(24) 0.8(2) no
C(22) C(21) C(20) C(25) 1.1(2) no
C(22) C(23) C(24) C(25) 0.7(2) no
