#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/34/1503409.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_1503409
loop_
_publ_author_name
'Yao, Wei'
'Huang, Dejian'
_publ_section_title
;
 Unexpected reactivity of o-nitrosophenol with RCH(2)Br: C-H bond cleavage
 and annulation to benzoxazoles and benzoxazines (R = Alkynyl).
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              736
_journal_page_last               738
_journal_paper_doi               10.1021/ol902812q
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.341(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3291(9)
_cell_length_b                   13.3826(14)
_cell_length_c                   15.8367(17)
_cell_measurement_reflns_used    4557
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      26.67
_cell_measurement_theta_min      2.59
_cell_volume                     1736.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12047
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0537
_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)+(0.0974P)²+0.1284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.1763
_reflns_number_gt                3024
_reflns_number_total             3976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902812q_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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_sg_symbol_H-M      P2(1)/n
_cod_database_code               1503409
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.81110(15) 0.55809(9) -0.15232(8) 0.0810(4) Uani 1 1 d .
H1 H 0.8078 0.5314 -0.1054 0.121 Uiso 1 1 calc R
O2 O 0.56257(12) 0.64794(8) 0.04241(6) 0.0670(3) Uani 1 1 d .
N1 N 0.73825(15) 0.53829(10) 0.00142(9) 0.0678(3) Uani 1 1 d .
N2 N 0.5802(2) 0.50046(12) 0.32582(9) 0.0844(4) Uani 1 1 d .
C1 C 0.5887(2) 0.77192(11) -0.25789(11) 0.0697(4) Uani 1 1 d .
C2 C 0.5764(3) 0.82232(13) -0.33739(12) 0.0836(5) Uani 1 1 d .
H2 H 0.5054 0.8771 -0.3492 0.100 Uiso 1 1 calc R
C3 C 0.6654(3) 0.79287(16) -0.39683(13) 0.0919(6) Uani 1 1 d .
H3 H 0.6567 0.8281 -0.4488 0.110 Uiso 1 1 calc R
C4 C 0.7698(3) 0.71074(16) -0.38153(12) 0.0888(5) Uani 1 1 d .
H4 H 0.8301 0.6909 -0.4235 0.107 Uiso 1 1 calc R
C5 C 0.7853(2) 0.65898(13) -0.30628(11) 0.0768(5) Uani 1 1 d .
H5 H 0.8560 0.6038 -0.2966 0.092 Uiso 1 1 calc R
C6 C 0.69491(19) 0.68835(11) -0.24285(10) 0.0660(4) Uani 1 1 d .
C7 C 0.70931(18) 0.63711(11) -0.16340(10) 0.0636(4) Uani 1 1 d .
C8 C 0.62405(17) 0.66874(11) -0.10071(9) 0.0614(4) Uani 1 1 d .
C9 C 0.51781(19) 0.75204(12) -0.11801(11) 0.0704(4) Uani 1 1 d .
H9 H 0.4582 0.7732 -0.0762 0.084 Uiso 1 1 calc R
C10 C 0.5005(2) 0.80180(12) -0.19374(11) 0.0758(4) Uani 1 1 d .
H10 H 0.4291 0.8567 -0.2037 0.091 Uiso 1 1 calc R
C11 C 0.64519(17) 0.61570(11) -0.02006(10) 0.0624(4) Uani 1 1 d .
C12 C 0.61026(17) 0.58218(11) 0.11012(10) 0.0633(4) Uani 1 1 d .
C13 C 0.71803(18) 0.51487(11) 0.08441(10) 0.0650(4) Uani 1 1 d .
C14 C 0.78670(19) 0.44238(12) 0.14302(12) 0.0733(4) Uani 1 1 d .
H14 H 0.8619 0.3958 0.1286 0.088 Uiso 1 1 calc R
C15 C 0.7420(2) 0.44057(12) 0.22198(11) 0.0734(4) Uani 1 1 d .
H15 H 0.7893 0.3920 0.2617 0.088 Uiso 1 1 calc R
C16 C 0.62811(19) 0.50818(12) 0.24708(10) 0.0692(4) Uani 1 1 d .
C17 C 0.56212(19) 0.58256(12) 0.18823(10) 0.0689(4) Uani 1 1 d .
H17 H 0.4882 0.6304 0.2020 0.083 Uiso 1 1 calc R
C18 C 0.4591(3) 0.56772(16) 0.35026(12) 0.0913(6) Uani 1 1 d .
H18A H 0.4071 0.5347 0.3936 0.110 Uiso 1 1 calc R
H18B H 0.3743 0.5803 0.2999 0.110 Uiso 1 1 calc R
C19 C 0.5266(3) 0.66423(19) 0.38473(15) 0.1156(8) Uani 1 1 d .
H19A H 0.6130 0.6526 0.4336 0.173 Uiso 1 1 calc R
H19B H 0.4409 0.7037 0.4027 0.173 Uiso 1 1 calc R
H19C H 0.5703 0.7000 0.3406 0.173 Uiso 1 1 calc R
C20 C 0.6493(3) 0.42513(17) 0.38870(13) 0.0955(6) Uani 1 1 d .
H20A H 0.6611 0.3622 0.3587 0.115 Uiso 1 1 calc R
H20B H 0.5733 0.4135 0.4282 0.115 Uiso 1 1 calc R
C21 C 0.8112(3) 0.4541(2) 0.43922(17) 0.1248(9) Uani 1 1 d .
H21A H 0.8857 0.4692 0.4004 0.187 Uiso 1 1 calc R
H21B H 0.8546 0.3994 0.4766 0.187 Uiso 1 1 calc R
H21C H 0.7986 0.5127 0.4735 0.187 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 O2 C12 104.27(11)
C11 N1 C13 105.00(13)
C16 N2 C18 121.39(14)
C16 N2 C20 121.68(17)
C18 N2 C20 116.93(16)
C10 C1 C2 122.69(16)
C10 C1 C6 119.40(15)
C2 C1 C6 117.91(16)
C3 C2 C1 121.15(19)
C2 C3 C4 120.61(18)
C5 C4 C3 120.63(19)
C4 C5 C6 120.03(18)
C5 C6 C7 121.62(15)
C5 C6 C1 119.65(15)
C7 C6 C1 118.72(14)
O1 C7 C8 122.53(14)
O1 C7 C6 116.48(14)
C8 C7 C6 120.98(14)
C7 C8 C9 118.90(14)
C7 C8 C11 119.11(13)
C9 C8 C11 121.99(14)
C10 C9 C8 121.34(15)
C9 C10 C1 120.63(15)
N1 C11 O2 114.45(13)
N1 C11 C8 126.48(14)
O2 C11 C8 119.07(13)
C17 C12 C13 125.44(14)
C17 C12 O2 127.34(13)
C13 C12 O2 107.22(13)
C12 C13 N1 109.05(13)
C12 C13 C14 117.91(16)
N1 C13 C14 133.00(15)
C15 C14 C13 118.37(15)
C14 C15 C16 123.40(15)
N2 C16 C17 120.66(16)
N2 C16 C15 121.47(15)
C17 C16 C15 117.85(16)
C12 C17 C16 116.99(15)
N2 C18 C19 113.83(19)
N2 C20 C21 113.21(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.3470(18)
O2 C11 1.3721(18)
O2 C12 1.3889(17)
N1 C11 1.3019(19)
N1 C13 1.391(2)
N2 C16 1.380(2)
N2 C18 1.455(3)
N2 C20 1.461(2)
C1 C10 1.414(2)
C1 C2 1.416(2)
C1 C6 1.419(2)
C2 C3 1.357(3)
C3 C4 1.396(3)
C4 C5 1.364(3)
C5 C6 1.415(2)
C6 C7 1.419(2)
C7 C8 1.387(2)
C8 C9 1.419(2)
C8 C11 1.444(2)
C9 C10 1.357(2)
C12 C17 1.367(2)
C12 C13 1.383(2)
C13 C14 1.392(2)
C14 C15 1.367(3)
C15 C16 1.419(2)
C16 C17 1.406(2)
C18 C19 1.474(3)
C20 C21 1.490(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 0.83 1.89 2.6262(17) 147.9
