#------------------------------------------------------------------------------
#$Date: 2016-03-04 10:27:09 +0200 (Fri, 04 Mar 2016) $
#$Revision: 177323 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/26/1542673.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_1542673
loop_
_publ_author_name
'Kumar, N. N. Bhuvan'
'Kutateladze, Andrei G.'
_publ_section_title
;
 Photoassisted Diversity-Oriented Synthesis: Intramolecular Cycloadditions
 of Photogenerated Azaxylylenes with Oxazole Pendants, and Subsequent
 Postphotochemical Multicomponent Modifications.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              460
_journal_page_last               463
_journal_paper_doi               10.1021/acs.orglett.5b03503
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C19 H13 Cl N2 O3'
_chemical_formula_sum            'C19 H13 Cl N2 O3'
_chemical_formula_weight         352.76
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 91.7860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.6228(3)
_cell_length_b                   12.8352(3)
_cell_length_c                   14.1014(2)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.29
_cell_measurement_theta_min      2.31
_cell_volume                     3188.08(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 APEX II Diffractometer'
_diffrn_measurement_method       'φ and ω 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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0094
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28709
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9234
_exptl_absorpt_correction_T_min  0.8143
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0541P)²+2.5525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                2622
_reflns_number_total             2915
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03503_si_003.cif
_cod_data_source_block           bkn45112
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               1542673
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.59249(3) 0.60161(4) -0.04323(4) 0.06258(18) Uani 1 1 d .
O1 O 0.63720(6) 0.20507(8) 0.26081(7) 0.0355(2) Uani 1 1 d .
O2 O 0.63977(7) -0.05336(9) 0.45699(7) 0.0464(3) Uani 1 1 d .
O3 O 0.50888(6) 0.13413(10) 0.10416(8) 0.0483(3) Uani 1 1 d .
N1 N 0.66614(7) 0.03669(9) 0.32037(8) 0.0332(3) Uani 1 1 d .
N2 N 0.74717(7) 0.12263(10) 0.21506(9) 0.0373(3) Uani 1 1 d .
C1 C 0.60248(10) 0.48303(13) 0.01622(13) 0.0462(4) Uani 1 1 d .
C2 C 0.60406(13) 0.48115(14) 0.11352(13) 0.0612(5) Uani 1 1 d .
H2 H 0.5996 0.5427 0.1477 0.073 Uiso 1 1 calc R
C3 C 0.61233(12) 0.38691(14) 0.16063(13) 0.0553(5) Uani 1 1 d .
H3 H 0.6140 0.3856 0.2266 0.066 Uiso 1 1 calc R
C4 C 0.61813(8) 0.29504(12) 0.11058(11) 0.0372(3) Uani 1 1 d .
C5 C 0.63160(8) 0.19211(11) 0.16025(10) 0.0337(3) Uani 1 1 d .
C6 C 0.69644(8) 0.13752(12) 0.29436(10) 0.0339(3) Uani 1 1 d .
C7 C 0.66432(8) 0.02264(12) 0.41742(10) 0.0363(3) Uani 1 1 d .
C8 C 0.60761(10) 0.39266(14) -0.03497(12) 0.0477(4) Uani 1 1 d .
H8 H 0.6061 0.3946 -0.1009 0.057 Uiso 1 1 calc R
C9 C 0.61499(10) 0.29861(13) 0.01224(12) 0.0441(4) Uani 1 1 d .
H9 H 0.6179 0.2371 -0.0223 0.053 Uiso 1 1 calc R
C10 C 0.56789(8) 0.11048(12) 0.14389(10) 0.0339(3) Uani 1 1 d .
C11 C 0.58213(8) 0.00102(11) 0.17793(9) 0.0314(3) Uani 1 1 d .
C12 C 0.54402(9) -0.07547(13) 0.12447(11) 0.0384(3) Uani 1 1 d .
H12 H 0.5111 -0.0550 0.0751 0.046 Uiso 1 1 calc R
C13 C 0.55362(9) -0.18014(13) 0.14254(12) 0.0431(4) Uani 1 1 d .
H13 H 0.5267 -0.2293 0.1066 0.052 Uiso 1 1 calc R
C14 C 0.60345(9) -0.21144(12) 0.21430(11) 0.0423(4) Uani 1 1 d .
H14 H 0.6113 -0.2820 0.2257 0.051 Uiso 1 1 calc R
C15 C 0.64163(9) -0.13829(12) 0.26918(11) 0.0380(3) Uani 1 1 d .
H15 H 0.6754 -0.1601 0.3171 0.046 Uiso 1 1 calc R
C16 C 0.63032(8) -0.03220(11) 0.25390(10) 0.0315(3) Uani 1 1 d .
C17 C 0.69650(11) 0.11850(14) 0.46405(11) 0.0490(4) Uani 1 1 d .
H17A H 0.7342 0.1001 0.5128 0.059 Uiso 1 1 calc R
H17B H 0.6567 0.1587 0.4929 0.059 Uiso 1 1 calc R
C18 C 0.73222(10) 0.17980(13) 0.38600(11) 0.0437(4) Uani 1 1 d .
H18A H 0.7868 0.1698 0.3873 0.052 Uiso 1 1 calc R
H18B H 0.7216 0.2535 0.3926 0.052 Uiso 1 1 calc R
C19 C 0.70947(8) 0.14812(12) 0.14112(10) 0.0349(3) Uani 1 1 d .
H19 H 0.7278 0.1406 0.0804 0.042 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 0.0016 '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'
Cl Cl 0.1484 0.1585 '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
C6 O1 C5 106.60(10)
C7 N1 C16 123.24(12)
C7 N1 C6 112.75(12)
C16 N1 C6 123.17(11)
C19 N2 C6 106.18(12)
C8 C1 C2 120.81(16)
C8 C1 Cl1 119.52(13)
C2 C1 Cl1 119.66(14)
C1 C2 C3 119.57(17)
C1 C2 H2 120.2
C3 C2 H2 120.2
C4 C3 C2 120.61(16)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C9 118.82(15)
C3 C4 C5 121.55(14)
C9 C4 C5 119.56(14)
O1 C5 C4 111.31(12)
O1 C5 C19 100.68(11)
C4 C5 C19 111.92(12)
O1 C5 C10 104.73(11)
C4 C5 C10 114.84(12)
C19 C5 C10 112.20(12)
O1 C6 N1 110.77(11)
O1 C6 N2 106.48(11)
N1 C6 N2 108.33(12)
O1 C6 C18 110.17(12)
N1 C6 C18 104.45(12)
N2 C6 C18 116.64(12)
O2 C7 N1 125.55(14)
O2 C7 C17 126.54(14)
N1 C7 C17 107.90(13)
C1 C8 C9 119.47(15)
C1 C8 H8 120.3
C9 C8 H8 120.3
C8 C9 C4 120.69(15)
C8 C9 H9 119.7
C4 C9 H9 119.7
O3 C10 C11 121.14(13)
O3 C10 C5 120.69(14)
C11 C10 C5 118.16(12)
C12 C11 C16 117.70(14)
C12 C11 C10 114.32(13)
C16 C11 C10 127.95(12)
C13 C12 C11 122.12(15)
C13 C12 H12 118.9
C11 C12 H12 118.9
C12 C13 C14 119.46(14)
C12 C13 H13 120.3
C14 C13 H13 120.3
C15 C14 C13 120.14(15)
C15 C14 H14 119.9
C13 C14 H14 119.9
C14 C15 C16 120.95(15)
C14 C15 H15 119.5
C16 C15 H15 119.5
C15 C16 C11 119.51(13)
C15 C16 N1 116.60(13)
C11 C16 N1 123.82(13)
C7 C17 C18 105.62(13)
C7 C17 H17A 110.6
C18 C17 H17A 110.6
C7 C17 H17B 110.6
C18 C17 H17B 110.6
H17A C17 H17B 108.7
C17 C18 C6 105.25(12)
C17 C18 H18A 110.7
C6 C18 H18A 110.7
C17 C18 H18B 110.7
C6 C18 H18B 110.7
H18A C18 H18B 108.8
N2 C19 C5 113.94(13)
N2 C19 H19 123.0
C5 C19 H19 123.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7438(17)
O1 C6 1.4265(18)
O1 C5 1.4281(17)
O2 C7 1.2104(19)
O3 C10 1.2046(18)
N1 C7 1.3817(18)
N1 C16 1.4220(18)
N1 C6 1.4514(19)
N2 C19 1.2619(19)
N2 C6 1.4659(19)
C1 C8 1.371(2)
C1 C2 1.372(3)
C2 C3 1.386(3)
C2 H2 0.9300
C3 C4 1.380(2)
C3 H3 0.9300
C4 C9 1.387(2)
C4 C5 1.511(2)
C5 C19 1.516(2)
C5 C10 1.548(2)
C6 C18 1.520(2)
C7 C17 1.498(2)
C8 C9 1.383(2)
C8 H8 0.9300
C9 H9 0.9300
C10 C11 1.503(2)
C11 C12 1.397(2)
C11 C16 1.412(2)
C12 C13 1.377(2)
C12 H12 0.9300
C13 C14 1.379(2)
C13 H13 0.9300
C14 C15 1.379(2)
C14 H14 0.9300
C15 C16 1.392(2)
C15 H15 0.9300
C17 C18 1.507(2)
C17 H17A 0.9700
C17 H17B 0.9700
C18 H18A 0.9700
C18 H18B 0.9700
C19 H19 0.9300
