#------------------------------------------------------------------------------
#$Date: 2015-05-18 07:26:09 +0300 (Mon, 18 May 2015) $
#$Revision: 136872 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/07/2240714.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240714
loop_
_publ_author_name
'Krishnamurthy, M. S.'
'Begum, Noor Shahina'
'Shamala, D.'
'Shivashankar, K.'
_publ_section_title
;
 Crystal structure of 4-azidomethyl-6-isopropyl-2H-chromen-2-one
;
_journal_coeditor_code           LH5754
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o227
_journal_page_last               o228
_journal_paper_doi               10.1107/S2056989015004387
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C13 H13 N3 O2'
_chemical_formula_moiety         'C13 H13 N3 O2'
_chemical_formula_sum            'C13 H13 N3 O2'
_chemical_formula_weight         243.26
_chemical_name_systematic
;
4-Azidomethyl-6-isopropyl-2H-chromen-2-one
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                72.218(6)
_cell_angle_beta                 79.662(5)
_cell_angle_gamma                82.430(6)
_cell_formula_units_Z            2
_cell_length_a                   6.895(2)
_cell_length_b                   7.862(2)
_cell_length_c                   11.592(4)
_cell_measurement_reflns_used    2028
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.87
_cell_volume                     586.7(3)
_computing_cell_refinement
;
SAINT (Bruker, 1998)
;
_computing_data_collection
;
SMART (Bruker, 1998)
;
_computing_data_reduction
;
SAINT (Bruker, 1998)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART APEX CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3059
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.865
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 1998)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0506
_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)+(0.0929P)²+0.0624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1498
_reflns_number_gt                1644
_reflns_number_total             2026
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5754sup1.cif
_cod_data_source_block           I
_cod_database_code               2240714
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O1 0.21989(18) 0.72869(15) 0.55787(11) 0.0218(4) Uani d 1
O O2 0.25015(19) 0.97173(16) 0.40014(12) 0.0275(4) Uani d 1
N N1 0.3566(3) 0.5078(2) 0.18653(14) 0.0295(4) Uani d 1
N N2 0.2838(2) 0.46732(19) 0.11032(14) 0.0224(4) Uani d 1
N N3 0.2296(3) 0.4459(2) 0.02953(15) 0.0347(5) Uani d 1
C C1 0.3110(3) 0.3983(2) 0.31451(15) 0.0208(4) Uani d 1
H H1A 0.4222 0.3069 0.3361 0.025 Uiso calc 1
H H1B 0.1911 0.3354 0.3245 0.025 Uiso calc 1
C C2 0.2481(3) 0.8106(2) 0.43304(16) 0.0215(4) Uani d 1
C C3 0.2742(3) 0.6957(2) 0.35451(16) 0.0206(4) Uani d 1
H H3 0.2898 0.7488 0.2683 0.025 Uiso calc 1
C C4 0.2773(2) 0.5161(2) 0.39858(16) 0.0185(4) Uani d 1
C C5 0.2560(2) 0.2462(2) 0.58662(16) 0.0190(4) Uani d 1
H H5 0.2745 0.1667 0.5374 0.023 Uiso calc 1
C C6 0.2339(3) 0.1765(2) 0.71344(16) 0.0197(4) Uani d 1
C C7 0.2029(3) 0.2955(2) 0.78447(17) 0.0223(4) Uani d 1
H H7 0.1848 0.2496 0.8712 0.027 Uiso calc 1
C C8 0.1980(3) 0.4781(2) 0.73103(16) 0.0212(4) Uani d 1
H H8 0.1781 0.5576 0.7803 0.025 Uiso calc 1
C C9 0.2226(2) 0.5440(2) 0.60513(16) 0.0190(4) Uani d 1
C C10 0.2516(2) 0.4322(2) 0.52983(16) 0.0175(4) Uani d 1
C C11 0.2405(3) -0.0239(2) 0.77465(16) 0.0231(5) Uani d 1
H H11 0.2825 -0.0853 0.7093 0.028 Uiso calc 1
C C12 0.3913(3) -0.0852(2) 0.86437(18) 0.0292(5) Uani d 1
H H12A 0.5230 -0.0542 0.8205 0.044 Uiso calc 1
H H12B 0.3927 -0.2152 0.9012 0.044 Uiso calc 1
H H12C 0.3546 -0.0253 0.9289 0.044 Uiso calc 1
C C13 0.0355(3) -0.0808(2) 0.83985(18) 0.0286(5) Uani d 1
H H13A -0.0161 -0.0113 0.8976 0.043 Uiso calc 1
H H13B 0.0457 -0.2087 0.8844 0.043 Uiso calc 1
H H13C -0.0542 -0.0588 0.7792 0.043 Uiso calc 1
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
C2 O1 C9 121.36(14)
N2 N1 C1 116.42(14)
N3 N2 N1 171.49(17)
N1 C1 C4 109.91(14)
N1 C1 H1A 109.7
C4 C1 H1A 109.7
N1 C1 H1B 109.7
C4 C1 H1B 109.7
H1A C1 H1B 108.2
O2 C2 O1 116.82(16)
O2 C2 C3 126.20(17)
O1 C2 C3 116.98(15)
C4 C3 C2 122.54(17)
C4 C3 H3 118.7
C2 C3 H3 118.7
C3 C4 C10 119.70(16)
C3 C4 C1 121.56(16)
C10 C4 C1 118.72(15)
C6 C5 C10 121.25(16)
C6 C5 H5 119.4
C10 C5 H5 119.4
C5 C6 C7 118.58(16)
C5 C6 C11 121.29(16)
C7 C6 C11 120.13(16)
C8 C7 C6 121.25(17)
C8 C7 H7 119.4
C6 C7 H7 119.4
C7 C8 C9 119.10(17)
C7 C8 H8 120.5
C9 C8 H8 120.5
C8 C9 O1 115.88(16)
C8 C9 C10 122.21(16)
O1 C9 C10 121.90(16)
C9 C10 C5 117.60(16)
C9 C10 C4 117.48(15)
C5 C10 C4 124.92(16)
C6 C11 C12 111.82(15)
C6 C11 C13 111.03(15)
C12 C11 C13 110.35(15)
C6 C11 H11 107.8
C12 C11 H11 107.8
C13 C11 H11 107.8
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.382(2)
O1 C9 1.386(2)
O2 C2 1.207(2)
N1 N2 1.228(2)
N1 C1 1.471(2)
N2 N3 1.133(2)
C1 C4 1.508(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.442(3)
C3 C4 1.346(2)
C3 H3 0.9500
C4 C10 1.450(2)
C5 C6 1.391(2)
C5 C10 1.407(2)
C5 H5 0.9500
C6 C7 1.398(3)
C6 C11 1.515(2)
C7 C8 1.378(2)
C7 H7 0.9500
C8 C9 1.378(3)
C8 H8 0.9500
C9 C10 1.391(3)
C11 C12 1.531(3)
C11 C13 1.532(3)
C11 H11 1.0000
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 O2 1_545 0.95 2.56 3.498(2) 168
C13 H13C O2 2_566 0.98 2.55 3.524(3) 172
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N2 N1 C1 C4 -140.65(17)
C9 O1 C2 O2 -177.52(15)
C9 O1 C2 C3 1.9(2)
O2 C2 C3 C4 177.40(17)
O1 C2 C3 C4 -1.9(3)
C2 C3 C4 C10 0.7(3)
C2 C3 C4 C1 -178.12(15)
N1 C1 C4 C3 5.5(2)
N1 C1 C4 C10 -173.34(14)
C10 C5 C6 C7 1.3(3)
C10 C5 C6 C11 -179.43(15)
C5 C6 C7 C8 -1.3(3)
C11 C6 C7 C8 179.40(15)
C6 C7 C8 C9 0.6(3)
C7 C8 C9 O1 -178.76(14)
C7 C8 C9 C10 0.2(3)
C2 O1 C9 C8 178.30(14)
C2 O1 C9 C10 -0.6(2)
C8 C9 C10 C5 -0.2(3)
O1 C9 C10 C5 178.68(14)
C8 C9 C10 C4 -179.50(15)
O1 C9 C10 C4 -0.6(2)
C6 C5 C10 C9 -0.5(3)
C6 C5 C10 C4 178.70(15)
C3 C4 C10 C9 0.6(2)
C1 C4 C10 C9 179.43(15)
C3 C4 C10 C5 -178.67(16)
C1 C4 C10 C5 0.2(2)
C5 C6 C11 C12 126.86(18)
C7 C6 C11 C12 -53.9(2)
C5 C6 C11 C13 -109.42(19)
C7 C6 C11 C13 69.9(2)

_cod_database_fobs_code 2240714
