#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/53/1505357.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_1505357
loop_
_publ_author_name
'Basavaiah, Deevi'
'Aravindu, Kunche'
_publ_section_title
;
 The Baylis-Hillman acetates as a valuable source for one-pot multistep
 synthesis: a facile synthesis of functionalized tri-/tetracyclic
 frameworks containing azocine moiety.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2453
_journal_page_last               2456
_journal_paper_doi               10.1021/ol070380u
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C20 H23 N O3, C4 H8 O2'
_chemical_formula_sum            'C24 H31 N O5'
_chemical_formula_weight         413.50
_chemical_melting_point          198(2)
_chemical_name_systematic
; 
2-Aza-5,5-dimethyl-10-ethoxycarbonyltricyclo[10.4.0.0(superscript 3,8)]
hexadeca-3(8),10,12,14,16-pentaen-7-one 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7778(4)
_cell_length_b                   14.5771(6)
_cell_length_c                   18.0574(8)
_cell_measurement_temperature    298
_cell_volume                     2310.53(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and 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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22350
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0494
_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)+(0.1134P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                1909
_reflns_number_total             2330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070380usi20070508_061713.cif
_cod_data_source_block           3
_cod_database_code               1505357
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
O1 O 0.4350(3) 0.31969(14) 0.23714(14) 0.0557(6) Uani 1 1 d .
O2 O 0.3407(6) 0.1170(3) 0.00363(17) 0.1083(14) Uani 1 1 d .
O3 O 0.3375(5) 0.24326(19) 0.06906(15) 0.0939(11) Uani 1 1 d .
O4 O 0.8139(6) 0.8804(4) 0.0195(3) 0.1479(18) Uani 1 1 d .
O5 O 0.6369(6) 0.7835(3) 0.0506(3) 0.1340(16) Uani 1 1 d .
N1 N 0.3956(3) -0.00559(15) 0.25834(15) 0.0439(6) Uani 1 1 d .
H1 H 0.4567 -0.0517 0.2568 0.053 Uiso 1 1 calc R
C1 C 0.2369(3) -0.02945(18) 0.25567(19) 0.0445(7) Uani 1 1 d .
C2 C 0.1745(4) -0.0690(2) 0.3177(2) 0.0551(9) Uani 1 1 d .
H2 H 0.2294 -0.0702 0.3618 0.066 Uiso 1 1 calc R
C3 C 0.0287(5) -0.1077(3) 0.3148(3) 0.0715(12) Uani 1 1 d .
H3 H -0.0142 -0.1332 0.3572 0.086 Uiso 1 1 calc R
C4 C -0.0501(4) -0.1078(3) 0.2500(3) 0.0764(13) Uani 1 1 d .
H4 H -0.1454 -0.1356 0.2475 0.092 Uiso 1 1 calc R
C5 C 0.0111(4) -0.0669(2) 0.1880(3) 0.0655(11) Uani 1 1 d .
H5 H -0.0441 -0.0674 0.1441 0.079 Uiso 1 1 calc R
C6 C 0.1531(4) -0.0251(2) 0.18959(19) 0.0485(8) Uani 1 1 d .
C7 C 0.2107(4) 0.0246(2) 0.12559(18) 0.0505(8) Uani 1 1 d .
H7 H 0.2146 -0.0053 0.0801 0.061 Uiso 1 1 calc R
C8 C 0.2580(4) 0.1113(2) 0.12956(17) 0.0465(7) Uani 1 1 d .
C9 C 0.2547(3) 0.16534(19) 0.20025(17) 0.0425(7) Uani 1 1 d .
H9A H 0.1736 0.1422 0.2316 0.051 Uiso 1 1 calc R
H9B H 0.2325 0.2290 0.1890 0.051 Uiso 1 1 calc R
C10 C 0.4043(3) 0.15975(19) 0.24169(16) 0.0384(7) Uani 1 1 d .
C11 C 0.4850(3) 0.24359(19) 0.25586(16) 0.0418(7) Uani 1 1 d .
C12 C 0.6356(4) 0.2380(2) 0.29601(19) 0.0488(8) Uani 1 1 d .
H12A H 0.6169 0.2389 0.3490 0.059 Uiso 1 1 calc R
H12B H 0.6958 0.2917 0.2838 0.059 Uiso 1 1 calc R
C13 C 0.7269(3) 0.1522(2) 0.27675(18) 0.0457(7) Uani 1 1 d .
C14 C 0.6239(3) 0.0703(2) 0.29415(18) 0.0441(7) Uani 1 1 d .
H14A H 0.6712 0.0152 0.2749 0.053 Uiso 1 1 calc R
H14B H 0.6166 0.0638 0.3475 0.053 Uiso 1 1 calc R
C15 C 0.4659(3) 0.07766(19) 0.26287(16) 0.0384(7) Uani 1 1 d .
C16 C 0.7739(4) 0.1531(3) 0.1965(2) 0.0589(9) Uani 1 1 d .
H16A H 0.6848 0.1554 0.1657 0.088 Uiso 1 1 calc R
H16B H 0.8309 0.0986 0.1855 0.088 Uiso 1 1 calc R
H16C H 0.8361 0.2061 0.1870 0.088 Uiso 1 1 calc R
C17 C 0.8701(4) 0.1472(3) 0.3258(2) 0.0631(9) Uani 1 1 d .
H17A H 0.9364 0.1975 0.3142 0.095 Uiso 1 1 calc R
H17B H 0.9223 0.0904 0.3169 0.095 Uiso 1 1 calc R
H17C H 0.8409 0.1505 0.3770 0.095 Uiso 1 1 calc R
C18 C 0.3166(5) 0.1548(3) 0.0603(2) 0.0628(10) Uani 1 1 d .
C19 C 0.3984(10) 0.2946(4) 0.0061(3) 0.121(2) Uani 1 1 d .
H19A H 0.4982 0.2715 -0.0072 0.145 Uiso 1 1 calc R
H19B H 0.3315 0.2884 -0.0363 0.145 Uiso 1 1 calc R
C20 C 0.4086(14) 0.3884(4) 0.0279(4) 0.162(4) Uani 1 1 d .
H20A H 0.3082 0.4121 0.0370 0.243 Uiso 1 1 calc R
H20B H 0.4560 0.4232 -0.0110 0.243 Uiso 1 1 calc R
H20C H 0.4684 0.3932 0.0722 0.243 Uiso 1 1 calc R
C21 C 0.5912(8) 0.9332(4) 0.0775(4) 0.124(2) Uani 1 1 d .
H21A H 0.6452 0.9698 0.1130 0.186 Uiso 1 1 calc R
H21B H 0.5068 0.9034 0.1013 0.186 Uiso 1 1 calc R
H21C H 0.5542 0.9717 0.0383 0.186 Uiso 1 1 calc R
C22 C 0.6916(6) 0.8654(4) 0.0475(3) 0.0855(14) Uani 1 1 d .
C23 C 0.7270(14) 0.7120(5) 0.0182(6) 0.205(5) Uani 1 1 d D
H23A H 0.8303 0.7340 0.0112 0.247 Uiso 1 1 calc R
H23B H 0.6859 0.6969 -0.0302 0.247 Uiso 1 1 calc R
C24 C 0.7303(13) 0.6302(4) 0.0633(4) 0.168(4) Uani 1 1 d D
H24A H 0.8125 0.6343 0.0981 0.251 Uiso 1 1 calc R
H24B H 0.7449 0.5775 0.0322 0.251 Uiso 1 1 calc R
H24C H 0.6356 0.6243 0.0895 0.251 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 0.0033 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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
C18 O3 C19 117.4(4)
C22 O5 C23 116.8(5)
C15 N1 C1 131.0(2)
C2 C1 C6 120.2(3)
C2 C1 N1 117.4(3)
C6 C1 N1 121.7(3)
C1 C2 C3 120.2(4)
C4 C3 C2 119.9(4)
C3 C4 C5 120.0(3)
C4 C5 C6 121.6(4)
C5 C6 C1 117.9(3)
C5 C6 C7 121.0(3)
C1 C6 C7 121.1(3)
C8 C7 C6 122.6(3)
C7 C8 C18 117.7(3)
C7 C8 C9 122.5(3)
C18 C8 C9 119.7(3)
C8 C9 C10 112.1(2)
C15 C10 C11 120.0(3)
C15 C10 C9 121.9(3)
C11 C10 C9 118.1(2)
O1 C11 C10 122.6(3)
O1 C11 C12 119.3(3)
C10 C11 C12 118.1(3)
C11 C12 C13 113.3(3)
C16 C13 C12 110.8(3)
C16 C13 C14 111.5(3)
C12 C13 C14 106.4(2)
C16 C13 C17 109.3(3)
C12 C13 C17 109.7(3)
C14 C13 C17 109.1(3)
C15 C14 C13 114.4(2)
N1 C15 C10 125.7(3)
N1 C15 C14 112.2(2)
C10 C15 C14 122.2(3)
O2 C18 O3 122.6(4)
O2 C18 C8 126.0(4)
O3 C18 C8 111.4(3)
C20 C19 O3 107.5(5)
O4 C22 O5 121.2(6)
O4 C22 C21 125.5(6)
O5 C22 C21 113.2(5)
O5 C23 C24 112.4(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.240(4)
O2 C18 1.182(5)
O3 C18 1.311(5)
O3 C19 1.462(5)
O4 C22 1.206(7)
O5 C22 1.288(7)
O5 C23 1.434(8)
N1 C15 1.364(4)
N1 C1 1.437(4)
C1 C2 1.375(5)
C1 C6 1.404(5)
C2 C3 1.399(5)
C3 C4 1.360(6)
C4 C5 1.377(6)
C5 C6 1.388(5)
C6 C7 1.455(5)
C7 C8 1.332(5)
C8 C18 1.494(5)
C8 C9 1.500(4)
C9 C10 1.513(4)
C10 C15 1.368(4)
C10 C11 1.436(4)
C11 C12 1.510(4)
C12 C13 1.526(4)
C13 C16 1.508(5)
C13 C14 1.530(4)
C13 C17 1.539(5)
C14 C15 1.501(4)
C19 C20 1.425(9)
C21 C22 1.430(8)
C23 C24 1.444(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651593
