#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/61/1506144.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_1506144
loop_
_publ_author_name
'Mandel, Sarah M.'
'Singh, Pradeep N. D.'
'Muthukrishnan, Sivaramakrishnan'
'Chang, Mingxin'
'Krause, Jeanette A.'
'Gudmundsdóttir, Anna D'
_publ_section_title
;
 Solid-state photolysis of alpha-azidoacetophenones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4207
_journal_page_last               4210
_journal_paper_doi               10.1021/ol061398s
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C14 H11 N3 O'
_chemical_formula_sum            'C14 H11 N3 O'
_chemical_formula_weight         237.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.9414(5)
_cell_length_b                   14.8154(13)
_cell_length_c                   26.690(2)
_cell_measurement_reflns_used    3111
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.75
_cell_volume                     2349.4(3)
_computing_cell_refinement       'SAINT v5.A06 (Bruker)'
_computing_data_collection       'SMART v4.050 (Bruker)'
_computing_data_reduction        'SAINT v5.A06 (Bruker)'
_computing_molecular_graphics    'SHELXTL v5.03 (Sheldrick)'
_computing_publication_material  'SHELXTL v5.03, 6.14 (Sheldrick)'
_computing_structure_refinement  'SHELXTL v5.03, 6.14 (Sheldrick)'
_computing_structure_solution    'SHELXTL v5.03 (Sheldrick)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 0.75
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1K CCD'
_diffrn_measurement_method       '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  0.0724
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14987
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9623
_exptl_absorpt_correction_T_min  0.8068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0450
_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)+(0.0469P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                1745
_reflns_number_total             2908
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol061398ssi20060608_024510.cif
_cod_data_source_block           1D
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

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_cell_volume        2349.4(4)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1506144
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'
'-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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O 0.0298(7) 0.0437(7) 0.0320(6) 0.0013(5) 0.0031(5) 0.0120(6)
N1 0.0369(8) 0.0247(7) 0.0316(7) -0.0011(6) 0.0030(7) -0.0054(6)
N2 0.0303(7) 0.0233(7) 0.0271(7) -0.0052(6) -0.0041(6) 0.0023(6)
N3 0.0404(9) 0.0525(9) 0.0345(8) -0.0079(7) 0.0057(7) -0.0029(8)
C1 0.0398(10) 0.0274(8) 0.0268(8) -0.0019(7) 0.0040(7) -0.0037(8)
C2 0.0334(10) 0.0285(8) 0.0280(8) 0.0022(7) -0.0059(7) -0.0027(7)
C3 0.0238(8) 0.0241(8) 0.0327(8) 0.0040(7) -0.0023(7) 0.0008(7)
C4 0.0248(8) 0.0175(7) 0.0240(7) 0.0038(6) 0.0012(6) -0.0002(6)
C5 0.0252(9) 0.0259(8) 0.0292(8) 0.0027(6) -0.0008(7) 0.0010(7)
C6 0.0275(9) 0.0305(9) 0.0333(9) -0.0013(7) 0.0051(7) 0.0019(7)
C7 0.0261(9) 0.0198(7) 0.0280(8) 0.0046(6) 0.0004(7) -0.0001(7)
C8 0.0242(8) 0.0232(7) 0.0246(7) -0.0005(6) 0.0014(6) -0.0012(6)
C9 0.0242(9) 0.0245(8) 0.0218(7) -0.0004(6) 0.0012(6) 0.0029(7)
C10 0.0255(9) 0.0417(9) 0.0318(9) 0.0015(8) -0.0008(7) 0.0010(8)
C11 0.0316(10) 0.0571(12) 0.0349(9) 0.0109(9) -0.0015(8) 0.0146(9)
C12 0.0495(12) 0.0352(10) 0.0338(9) 0.0115(7) 0.0110(9) 0.0171(9)
C13 0.0460(12) 0.0261(9) 0.0426(10) 0.0064(8) 0.0041(9) -0.0025(8)
C14 0.0273(9) 0.0276(8) 0.0347(9) 0.0035(7) -0.0028(7) -0.0005(7)
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O O 0.1481(2) 0.96377(7) 0.09758(4) 0.0352(3) Uani 1 d .
N1 N 0.4722(2) 1.00623(8) 0.16575(5) 0.0310(3) Uani 1 d .
N2 N 0.3213(2) 0.98385(8) 0.19491(5) 0.0269(3) Uani 1 d .
N3 N 0.1899(3) 0.97127(10) 0.22499(5) 0.0424(4) Uani 1 d .
C1 C 0.4693(3) 0.84019(10) -0.06120(6) 0.0313(4) Uani 1 d .
H1 H 0.4976 0.81952 -0.09430 0.038 Uiso 1 calc R
C2 C 0.2621(3) 0.87702(10) -0.04921(6) 0.0299(4) Uani 1 d .
H2 H 0.1479 0.88154 -0.07400 0.036 Uiso 1 calc R
C3 C 0.2221(3) 0.90716(10) -0.00110(6) 0.0269(4) Uani 1 d .
H3 H 0.0789 0.93156 0.00714 0.032 Uiso 1 calc R
C4 C 0.3889(3) 0.90230(9) 0.03562(5) 0.0221(3) Uani 1 d .
C5 C 0.5964(3) 0.86480(10) 0.02318(5) 0.0268(4) Uani 1 d .
H5 H 0.7117 0.86068 0.04775 0.032 Uiso 1 calc R
C6 C 0.6353(3) 0.83342(11) -0.02506(6) 0.0305(4) Uani 1 d .
H6 H 0.7764 0.80720 -0.03329 0.037 Uiso 1 calc R
C7 C 0.3360(3) 0.93752(9) 0.08658(6) 0.0246(3) Uani 1 d .
C8 C 0.5233(3) 0.93885(9) 0.12623(5) 0.0240(3) Uani 1 d .
H8 H 0.6651 0.95835 0.10920 0.029 Uiso 1 calc R
C9 C 0.5642(3) 0.84509(10) 0.14788(5) 0.0235(3) Uani 1 d .
C10 C 0.7682(3) 0.82737(12) 0.17141(6) 0.0330(4) Uani 1 d .
H10 H 0.8810 0.87274 0.17286 0.040 Uiso 1 calc R
C11 C 0.8070(3) 0.74341(13) 0.19277(6) 0.0412(5) Uani 1 d .
H11 H 0.9459 0.73198 0.20925 0.049 Uiso 1 calc R
C12 C 0.6465(3) 0.67644(12) 0.19033(6) 0.0395(5) Uani 1 d .
H12 H 0.6752 0.61878 0.20454 0.047 Uiso 1 calc R
C13 C 0.4442(3) 0.69382(11) 0.16714(6) 0.0382(4) Uani 1 d .
H13 H 0.3325 0.64804 0.16541 0.046 Uiso 1 calc R
C14 C 0.4029(3) 0.77791(10) 0.14632(6) 0.0299(4) Uani 1 d .
H14 H 0.2620 0.78953 0.13078 0.036 Uiso 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
N2 N1 C8 114.62(12)
N3 N2 N1 172.25(15)
C6 C1 C2 120.10(14)
C3 C2 C1 119.73(15)
C2 C3 C4 120.95(15)
C5 C4 C3 118.81(13)
C5 C4 C7 122.97(13)
C3 C4 C7 118.22(13)
C6 C5 C4 120.13(14)
C1 C6 C5 120.27(15)
O C7 C4 121.69(14)
O C7 C8 119.58(13)
C4 C7 C8 118.72(13)
N1 C8 C9 112.11(11)
N1 C8 C7 110.52(12)
C9 C8 C7 111.42(12)
C14 C9 C10 118.84(14)
C14 C9 C8 122.27(13)
C10 C9 C8 118.86(14)
C11 C10 C9 120.0(2)
C12 C11 C10 120.7(2)
C13 C12 C11 119.4(2)
C12 C13 C14 120.2(2)
C9 C14 C13 120.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C7 1.218(2)
N1 N2 1.233(2)
N1 C8 1.483(2)
N2 N3 1.135(2)
C1 C6 1.383(2)
C1 C2 1.384(2)
C2 C3 1.380(2)
C3 C4 1.396(2)
C4 C5 1.393(2)
C4 C7 1.490(2)
C5 C6 1.388(2)
C7 C8 1.536(2)
C8 C9 1.524(2)
C9 C14 1.383(2)
C9 C10 1.390(2)
C10 C11 1.388(2)
C11 C12 1.378(3)
C12 C13 1.376(2)
C13 C14 1.386(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3433492
