#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:34:10 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180145 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/42/7104245.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_7104245
loop_
_publ_author_name
'Satyanarayana, Gedu'
'Maichle-Mössmer, Caecilia'
'Maier, Martin E'
_publ_section_title
;
 Formation of pentacyclic structures by a domino sequence on cyclic
 enamides.
;
_journal_issue                   12
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1571
_journal_page_last               1573
_journal_paper_doi               10.1039/b820636h
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C21 H21 N O'
_chemical_formula_weight         303.39
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.156(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3172(13)
_cell_length_b                   7.6048(6)
_cell_length_c                   18.468(2)
_cell_measurement_reflns_used    16237
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.44
_cell_measurement_theta_min      4.05
_cell_volume                     1541.2(3)
_computing_cell_refinement       x-Area
_computing_data_collection       'Stoe IPDSII'
_computing_data_reduction        X-Area
_computing_molecular_graphics    'SCHAKAL, ZORTEP'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Stoe IPDSII'
_diffrn_measurement_method       omega-Scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21754
_diffrn_reflns_theta_full        26.77
_diffrn_reflns_theta_max         26.77
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bloc
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    iso
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0519
_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)+(0.0343P)²+0.8361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                2821
_reflns_number_total             3269
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b820636h.txt
_cod_data_source_block           maigs149b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.8361P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.8361P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7104245
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.04402(14) 0.5160(2) -0.11091(9) 0.0188(3) Uani 1 d . . .
C2 C 0.00808(16) 0.3777(2) -0.16073(10) 0.0254(4) Uani 1 d . . .
H2 H 0.0439(19) 0.261(3) -0.1510(11) 0.029(5) Uiso 1 d . . .
C3 C -0.08166(16) 0.4079(3) -0.22600(10) 0.0283(4) Uani 1 d . . .
H31 H -0.1045(19) 0.314(3) -0.2597(12) 0.033(6) Uiso 1 d . . .
C4 C -0.13587(16) 0.5723(3) -0.24088(10) 0.0284(4) Uani 1 d . . .
H4 H -0.197(2) 0.591(3) -0.2854(13) 0.037(6) Uiso 1 d . . .
C5 C -0.10022(16) 0.7105(2) -0.19115(10) 0.0254(4) Uani 1 d . . .
H5 H -0.1371(19) 0.825(3) -0.2007(12) 0.030(5) Uiso 1 d . . .
C6 C -0.00930(14) 0.6810(2) -0.12639(9) 0.0196(3) Uani 1 d . . .
C7 C 0.04298(15) 0.8094(2) -0.06495(10) 0.0213(3) Uani 1 d . . .
H7A H -0.0199(17) 0.854(2) -0.0410(10) 0.019(5) Uiso 1 d . . .
H7B H 0.0849(18) 0.911(3) -0.0839(11) 0.025(5) Uiso 1 d . . .
N8 N 0.13210(12) 0.70032(18) -0.01301(8) 0.0196(3) Uani 1 d . . .
C9 C 0.13250(14) 0.5138(2) -0.03513(9) 0.0172(3) Uani 1 d . . .
H9 H 0.0972(16) 0.444(2) 0.0013(10) 0.016(4) Uiso 1 d . . .
C10 C 0.19385(15) 0.7533(2) 0.05558(9) 0.0203(3) Uani 1 d . . .
C11 C 0.28288(16) 0.6154(2) 0.09499(9) 0.0225(4) Uani 1 d . . .
H11A H 0.3395(18) 0.671(3) 0.1369(11) 0.024(5) Uiso 1 d . . .
H11B H 0.2380(19) 0.522(3) 0.1157(12) 0.032(5) Uiso 1 d . . .
C12 C 0.35005(15) 0.5367(2) 0.03957(9) 0.0205(3) Uani 1 d . . .
H12A H 0.3901(18) 0.635(3) 0.0199(11) 0.022(5) Uiso 1 d . . .
H12B H 0.4159(18) 0.455(3) 0.0662(11) 0.022(5) Uiso 1 d . . .
C13 C 0.26390(14) 0.4369(2) -0.02604(9) 0.0171(3) Uani 1 d . . .
C14 C 0.31022(14) 0.4571(2) -0.09680(9) 0.0183(3) Uani 1 d . . .
C15 C 0.35399(14) 0.3143(2) -0.13032(9) 0.0201(3) Uani 1 d . . .
C16 C 0.35868(17) 0.1300(2) -0.09870(11) 0.0269(4) Uani 1 d . . .
H16A H 0.285(2) 0.062(3) -0.1261(13) 0.037(6) Uiso 1 d . . .
H16B H 0.431(2) 0.069(3) -0.1082(12) 0.036(6) Uiso 1 d . . .
C17 C 0.36179(16) 0.1323(2) -0.01611(10) 0.0248(4) Uani 1 d . . .
H17A H 0.3555(19) 0.015(3) 0.0021(12) 0.031(5) Uiso 1 d . . .
H17B H 0.4421(19) 0.183(3) 0.0131(11) 0.026(5) Uiso 1 d . . .
C18 C 0.25576(15) 0.2421(2) -0.00437(10) 0.0210(3) Uani 1 d . . .
H18A H 0.1781(18) 0.189(3) -0.0350(11) 0.023(5) Uiso 1 d . . .
H18B H 0.2503(17) 0.237(2) 0.0492(11) 0.021(5) Uiso 1 d . . .
C19 C 0.31266(15) 0.6248(2) -0.12797(10) 0.0226(4) Uani 1 d . . .
H19 H 0.2838(19) 0.729(3) -0.1033(12) 0.030(5) Uiso 1 d . . .
C20 C 0.35649(16) 0.6513(3) -0.19087(10) 0.0272(4) Uani 1 d . . .
H20 H 0.3561(19) 0.766(3) -0.2118(12) 0.028(5) Uiso 1 d . . .
C21 C 0.39928(17) 0.5085(3) -0.22419(10) 0.0292(4) Uani 1 d . . .
H21 H 0.433(2) 0.525(3) -0.2690(12) 0.035(6) Uiso 1 d . . .
C22 C 0.39727(16) 0.3428(3) -0.19426(10) 0.0261(4) Uani 1 d . . .
H22 H 0.4249(19) 0.243(3) -0.2175(12) 0.031(5) Uiso 1 d . . .
O23 O 0.18183(11) 0.90045(16) 0.08031(7) 0.0272(3) Uani 1 d . . .
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'
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'
H H 0.0000 0.0000 '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
C2 C1 C6 120.26(15) . . ?
C2 C1 C9 128.74(15) . . ?
C6 C1 C9 110.89(14) . . ?
C1 C2 C3 118.76(17) . . ?
C4 C3 C2 120.86(17) . . ?
C5 C4 C3 120.44(16) . . ?
C4 C5 C6 118.72(17) . . ?
C1 C6 C5 120.94(16) . . ?
C1 C6 C7 111.08(14) . . ?
C5 C6 C7 127.97(16) . . ?
N8 C7 C6 101.95(13) . . ?
C10 N8 C7 124.06(14) . . ?
C10 N8 C9 120.71(13) . . ?
C7 N8 C9 114.22(13) . . ?
N8 C9 C1 101.54(12) . . ?
N8 C9 C13 113.30(13) . . ?
C1 C9 C13 120.02(13) . . ?
O23 C10 N8 122.82(15) . . ?
O23 C10 C11 125.04(15) . . ?
N8 C10 C11 112.05(14) . . ?
C10 C11 C12 109.23(14) . . ?
C11 C12 C13 113.01(13) . . ?
C14 C13 C18 111.84(13) . . ?
C14 C13 C12 109.66(12) . . ?
C18 C13 C12 109.40(13) . . ?
C14 C13 C9 112.66(12) . . ?
C18 C13 C9 105.69(12) . . ?
C12 C13 C9 107.41(12) . . ?
C15 C14 C19 118.65(15) . . ?
C15 C14 C13 122.20(14) . . ?
C19 C14 C13 119.12(14) . . ?
C14 C15 C22 119.18(15) . . ?
C14 C15 C16 122.03(15) . . ?
C22 C15 C16 118.78(15) . . ?
C15 C16 C17 111.54(14) . . ?
C16 C17 C18 108.95(14) . . ?
C17 C18 C13 113.01(13) . . ?
C20 C19 C14 121.57(16) . . ?
C19 C20 C21 119.47(17) . . ?
C22 C21 C20 119.62(16) . . ?
C21 C22 C15 121.51(16) . . ?
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
C1 C2 1.391(2) . ?
C1 C6 1.391(2) . ?
C1 C9 1.509(2) . ?
C2 C3 1.392(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.392(2) . ?
C6 C7 1.504(2) . ?
C7 N8 1.467(2) . ?
N8 C10 1.350(2) . ?
N8 C9 1.476(2) . ?
C9 C13 1.568(2) . ?
C10 O23 1.228(2) . ?
C10 C11 1.512(2) . ?
C11 C12 1.538(2) . ?
C12 C13 1.554(2) . ?
C13 C14 1.530(2) . ?
C13 C18 1.544(2) . ?
C14 C15 1.399(2) . ?
C14 C19 1.403(2) . ?
C15 C22 1.401(2) . ?
C15 C16 1.514(2) . ?
C16 C17 1.517(3) . ?
C17 C18 1.520(2) . ?
C19 C20 1.385(2) . ?
C20 C21 1.392(3) . ?
C21 C22 1.378(3) . ?
