#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/87/1508794.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_1508794
loop_
_publ_author_name
'Huang, Liping'
'Liu, Yang'
'Xie, Fuchun'
'Hu, Youhong'
_publ_section_title
;
 An organic molecule modulated chemoselective cyclization of alkynyl
 nitriles tethered to 2-alkyl substituted chromones with multireactive
 sites.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6122
_journal_page_last               6125
_journal_paper_doi               10.1021/ol302964x
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C25 H22 N2 O2'
_chemical_formula_weight         382.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.286(2)
_cell_angle_beta                 75.763(2)
_cell_angle_gamma                82.041(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5967(8)
_cell_length_b                   10.5041(9)
_cell_length_c                   12.0568(11)
_cell_measurement_reflns_used    8118
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      33.01
_cell_measurement_theta_min      2.33
_cell_volume                     1008.02(16)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15919
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0403
_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)+(0.0654P)²+0.3102P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                3727
_reflns_number_total             4381
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302964x_si_002.cif
_cod_data_source_block           mo_dm11206_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1508794
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.1861(3) 0.84657(16) 0.7650(2) 0.0892(7) Uani 1 1 d .
N2 N 0.62316(17) 0.35621(16) 0.87729(12) 0.0502(4) Uani 1 1 d .
O1 O -0.03503(9) 0.58629(8) 0.67162(7) 0.02237(19) Uani 1 1 d .
O2 O -0.34038(11) 0.39381(9) 0.57367(8) 0.0304(2) Uani 1 1 d .
C1 C -0.17163(13) 0.65236(11) 0.63794(10) 0.0211(2) Uani 1 1 d .
C2 C -0.19816(15) 0.78540(12) 0.64095(11) 0.0265(3) Uani 1 1 d .
H2 H -0.1242 0.8258 0.6649 0.032 Uiso 1 1 calc R
C3 C -0.33444(16) 0.85722(13) 0.60832(12) 0.0303(3) Uani 1 1 d .
H3 H -0.3551 0.9477 0.6107 0.036 Uiso 1 1 calc R
C4 C -0.44219(15) 0.79813(13) 0.57190(12) 0.0302(3) Uani 1 1 d .
H4 H -0.5353 0.8486 0.5494 0.036 Uiso 1 1 calc R
C5 C -0.41373(14) 0.66686(12) 0.56858(10) 0.0257(3) Uani 1 1 d .
H5 H -0.4867 0.6274 0.5429 0.031 Uiso 1 1 calc R
C6 C -0.27708(13) 0.59102(12) 0.60304(10) 0.0215(2) Uani 1 1 d .
C7 C -0.24543(14) 0.45028(11) 0.60130(10) 0.0221(2) Uani 1 1 d .
C8 C -0.09558(13) 0.38360(11) 0.63585(10) 0.0199(2) Uani 1 1 d .
C9 C -0.04524(14) 0.24885(11) 0.63788(10) 0.0222(2) Uani 1 1 d .
C10 C 0.09593(14) 0.19496(11) 0.67381(10) 0.0228(2) Uani 1 1 d .
H10 H 0.1293 0.1044 0.6757 0.027 Uiso 1 1 calc R
C11 C 0.19207(13) 0.26845(11) 0.70765(10) 0.0208(2) Uani 1 1 d .
C12 C 0.14591(13) 0.40108(11) 0.70631(9) 0.0198(2) Uani 1 1 d .
C13 C 0.00212(13) 0.45507(11) 0.67040(9) 0.0192(2) Uani 1 1 d .
C14 C -0.13889(16) 0.16160(12) 0.60174(12) 0.0298(3) Uani 1 1 d .
H14A H -0.0807 0.0738 0.6064 0.045 Uiso 1 1 calc R
H14B H -0.1514 0.2029 0.5202 0.045 Uiso 1 1 calc R
H14C H -0.2452 0.1515 0.6552 0.045 Uiso 1 1 calc R
C15 C 0.34424(14) 0.19907(12) 0.74726(10) 0.0229(2) Uani 1 1 d .
H15A H 0.3768 0.1191 0.7168 0.028 Uiso 1 1 calc R
H15B H 0.4323 0.2599 0.7133 0.028 Uiso 1 1 calc R
C16 C 0.31894(14) 0.15845(12) 0.88004(11) 0.0262(3) Uani 1 1 d .
C17 C 0.18469(19) 0.07370(16) 0.95666(13) 0.0427(4) Uani 1 1 d .
H17A H 0.1887 -0.0088 0.9317 0.051 Uiso 1 1 calc R
H17B H 0.0787 0.1231 0.9520 0.051 Uiso 1 1 calc R
C18 C 0.2133(2) 0.04117(17) 1.08215(13) 0.0473(4) Uani 1 1 d .
H18A H 0.2566 -0.0525 1.1069 0.057 Uiso 1 1 calc R
H18B H 0.1113 0.0541 1.1389 0.057 Uiso 1 1 calc R
C19 C 0.3346(2) 0.13630(18) 1.07899(13) 0.0470(4) Uani 1 1 d .
H19A H 0.2816 0.2075 1.1172 0.056 Uiso 1 1 calc R
H19B H 0.4215 0.0880 1.1190 0.056 Uiso 1 1 calc R
C20 C 0.39926(15) 0.19293(13) 0.94760(11) 0.0304(3) Uani 1 1 d .
C21 C 0.52491(17) 0.28236(15) 0.90553(12) 0.0356(3) Uani 1 1 d .
C22 C 0.24079(14) 0.48929(11) 0.73996(10) 0.0230(2) Uani 1 1 d .
H22A H 0.2429 0.5780 0.6821 0.028 Uiso 1 1 calc R
H22B H 0.3531 0.4504 0.7354 0.028 Uiso 1 1 calc R
C23 C 0.17049(16) 0.50623(13) 0.86504(11) 0.0297(3) Uani 1 1 d .
H23A H 0.0545 0.5347 0.8730 0.036 Uiso 1 1 calc R
H23B H 0.1811 0.4194 0.9239 0.036 Uiso 1 1 calc R
C24 C 0.2559(2) 0.60927(16) 0.89141(16) 0.0474(4) Uani 1 1 d .
H24A H 0.2214 0.6060 0.9767 0.057 Uiso 1 1 calc R
H24B H 0.3736 0.5872 0.8736 0.057 Uiso 1 1 calc R
C25 C 0.2194(2) 0.74342(17) 0.82073(19) 0.0547(5) Uani 1 1 d .
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
C1 O1 C13 120.01(9)
O1 C1 C6 122.16(10)
O1 C1 C2 115.80(10)
C6 C1 C2 122.03(11)
C3 C2 C1 118.48(11)
C3 C2 H2 120.8
C1 C2 H2 120.8
C2 C3 C4 120.68(11)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 120.16(11)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 120.26(11)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 118.38(11)
C1 C6 C7 120.53(10)
C5 C6 C7 121.09(10)
O2 C7 C6 121.09(11)
O2 C7 C8 123.33(11)
C6 C7 C8 115.58(10)
C13 C8 C9 117.68(10)
C13 C8 C7 119.13(10)
C9 C8 C7 123.19(10)
C10 C9 C8 118.66(10)
C10 C9 C14 118.52(10)
C8 C9 C14 122.82(10)
C9 C10 C11 122.70(10)
C9 C10 H10 118.6
C11 C10 H10 118.6
C12 C11 C10 119.95(10)
C12 C11 C15 121.53(10)
C10 C11 C15 118.51(10)
C11 C12 C13 117.12(10)
C11 C12 C22 124.28(10)
C13 C12 C22 118.60(10)
O1 C13 C12 113.54(9)
O1 C13 C8 122.57(10)
C12 C13 C8 123.90(10)
C9 C14 H14A 109.5
C9 C14 H14B 109.5
H14A C14 H14B 109.5
C9 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C16 C15 C11 111.34(9)
C16 C15 H15A 109.4
C11 C15 H15A 109.4
C16 C15 H15B 109.4
C11 C15 H15B 109.4
H15A C15 H15B 108.0
C20 C16 C15 128.25(11)
C20 C16 C17 110.26(12)
C15 C16 C17 121.42(11)
C16 C17 C18 104.91(12)
C16 C17 H17A 110.8
C18 C17 H17A 110.8
C16 C17 H17B 110.8
C18 C17 H17B 110.8
H17A C17 H17B 108.8
C17 C18 C19 106.60(12)
C17 C18 H18A 110.4
C19 C18 H18A 110.4
C17 C18 H18B 110.4
C19 C18 H18B 110.4
H18A C18 H18B 108.6
C20 C19 C18 103.10(12)
C20 C19 H19A 111.1
C18 C19 H19A 111.1
C20 C19 H19B 111.1
C18 C19 H19B 111.1
H19A C19 H19B 109.1
C16 C20 C21 125.67(12)
C16 C20 C19 112.98(13)
C21 C20 C19 121.16(12)
N2 C21 C20 176.34(15)
C12 C22 C23 112.67(9)
C12 C22 H22A 109.1
C23 C22 H22A 109.1
C12 C22 H22B 109.1
C23 C22 H22B 109.1
H22A C22 H22B 107.8
C24 C23 C22 111.68(12)
C24 C23 H23A 109.3
C22 C23 H23A 109.3
C24 C23 H23B 109.3
C22 C23 H23B 109.3
H23A C23 H23B 107.9
C25 C24 C23 111.11(13)
C25 C24 H24A 109.4
C23 C24 H24A 109.4
C25 C24 H24B 109.4
C23 C24 H24B 109.4
H24A C24 H24B 108.0
N1 C25 C24 177.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C25 1.139(3)
N2 C21 1.149(2)
O1 C1 1.3683(14)
O1 C13 1.3745(13)
O2 C7 1.2291(14)
C1 C6 1.3855(16)
C1 C2 1.3939(16)
C2 C3 1.3811(18)
C2 H2 0.9500
C3 C4 1.3972(19)
C3 H3 0.9500
C4 C5 1.3771(18)
C4 H4 0.9500
C5 C6 1.4063(16)
C5 H5 0.9500
C6 C7 1.4709(16)
C7 C8 1.4730(16)
C8 C13 1.4033(15)
C8 C9 1.4167(16)
C9 C10 1.3814(17)
C9 C14 1.5115(15)
C10 C11 1.4033(16)
C10 H10 0.9500
C11 C12 1.3914(16)
C11 C15 1.5210(16)
C12 C13 1.4017(16)
C12 C22 1.5089(15)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 C16 1.5013(16)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C20 1.3369(18)
C16 C17 1.5049(18)
C17 C18 1.526(2)
C17 H17A 0.9900
C17 H17B 0.9900
C18 C19 1.528(2)
C18 H18A 0.9900
C18 H18B 0.9900
C19 C20 1.5129(19)
C19 H19A 0.9900
C19 H19B 0.9900
C20 C21 1.430(2)
C22 C23 1.5321(17)
C22 H22A 0.9900
C22 H22B 0.9900
C23 C24 1.5314(18)
C23 H23A 0.9900
C23 H23B 0.9900
C24 C25 1.459(3)
C24 H24A 0.9900
C24 H24B 0.9900
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30652077 ChemSpider
