#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:18:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178429 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/50/4025040.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_4025040
loop_
_publ_author_name
'Jui-Chi Tsai'
'Sie-Rong Li'
'Michael Y. Chiang'
'Lian-Yeu Chen'
'Po-Yuan Chen'
'Yi-Fang Lo'
'Chen-Hao Wang'
'Chun-Nan Lin'
'Eng-Chi Wang'
_publ_section_title
;
Synthesis of 3-Alkoxymethylcoumarin from 3-Cyanochromene via a Novel
Intermediate 2-Phenylimino-3-alkoxymethylchromene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8798
_journal_page_last               8801
_journal_paper_doi               10.1021/jo9015634
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 101.068(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.856(2)
_cell_length_b                   7.3947(18)
_cell_length_c                   11.096(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.17
_cell_measurement_theta_min      8.45
_cell_volume                     793.7(3)
_computing_cell_refinement
'MSC/AFC (Molecular Structure Corporation, 1992)'
_computing_data_collection
'MSC/AFC (Molecular Structure Corporation, 1992)'
_computing_data_reduction
'teXsan (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC7S'
_diffrn_measurement_method       2θ/ω
_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  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1769
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        -0.34
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.177(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0409
_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)+(0.0660P)²+0.1743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                1332
_reflns_number_total             1685
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9015634_si_001.cif
_cod_data_source_block           ecw1a
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4025040
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55265(13) 0.2500 0.79236(11) 0.0483(4) Uani 1 2 d S . .
O2 O 0.50854(15) 0.2500 1.21636(12) 0.0545(5) Uani 1 2 d S . .
N1 N 0.33784(17) 0.2500 0.84177(15) 0.0503(5) Uani 1 2 d S . .
C1 C 0.46780(19) 0.2500 0.87719(17) 0.0413(5) Uani 1 2 d S . .
C2 C 0.53127(19) 0.2500 1.00723(17) 0.0421(5) Uani 1 2 d S . .
C3 C 0.6685(2) 0.2500 1.04118(18) 0.0486(5) Uani 1 2 d S . .
H3 H 0.7079 0.2500 1.1243 0.058 Uiso 1 2 calc SR . .
C4 C 0.7572(2) 0.2500 0.95171(18) 0.0467(5) Uani 1 2 d S . .
C5 C 0.9017(2) 0.2500 0.9802(2) 0.0659(7) Uani 1 2 d S . .
H5 H 0.9463 0.2500 1.0620 0.079 Uiso 1 2 calc SR . .
C7 C 0.9138(2) 0.2500 0.7676(2) 0.0572(6) Uani 1 2 d S . .
H7 H 0.9663 0.2500 0.7063 0.069 Uiso 1 2 calc SR . .
C8 C 0.7711(2) 0.2500 0.73614(19) 0.0524(6) Uani 1 2 d S . .
H8 H 0.7271 0.2500 0.6541 0.063 Uiso 1 2 calc SR . .
C9 C 0.69488(19) 0.2500 0.82795(17) 0.0426(5) Uani 1 2 d S . .
C10 C 0.4331(2) 0.2500 1.09498(18) 0.0467(5) Uani 1 2 d S . .
C11 C 0.4213(2) 0.2500 1.3041(2) 0.0578(6) Uani 1 2 d S . .
C12 C 0.5060(3) 0.2500 1.4300(2) 0.0707(8) Uani 1 2 d S . .
C6 C 0.9788(2) 0.2500 0.8894(2) 0.0669(7) Uani 1 2 d S . .
H6 H 1.0748 0.2500 0.9100 0.080 Uiso 1 2 calc SR . .
C13 C 0.27706(18) 0.2500 0.71452(17) 0.0454(5) Uani 1 2 d S . .
C14 C 0.24173(15) 0.0896(2) 0.65328(13) 0.0534(4) Uani 1 1 d . . .
H14 H 0.2653 -0.0198 0.6931 0.064 Uiso 1 1 calc R . .
C15 C 0.17098(15) 0.0907(2) 0.53224(13) 0.0547(4) Uani 1 1 d . . .
H15 H 0.1480 -0.0188 0.4923 0.066 Uiso 1 1 calc R . .
C16 C 0.1338(2) 0.2500 0.46972(18) 0.0485(5) Uani 1 2 d S . .
C17 C 0.0550(3) 0.2500 0.3391(2) 0.0624(7) Uani 1 2 d S . .
H10A H 0.3722(19) 0.138(3) 1.0811(16) 0.080 Uiso 1 1 d . . .
H11A H 0.363(2) 0.141(3) 1.2921(17) 0.080 Uiso 1 1 d . . .
H12A H 0.450(3) 0.2500 1.494(3) 0.080 Uiso 1 2 d S . .
H12B H 0.569(2) 0.149(3) 1.4405(17) 0.080 Uiso 1 1 d . . .
H17A H -0.041(3) 0.2500 0.339(3) 0.080 Uiso 1 2 d S . .
H17B H 0.073(2) 0.152(3) 0.2960(17) 0.080 Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 121.46(14) . . ?
C10 O2 C11 112.26(16) . . ?
C1 N1 C13 121.06(16) . . ?
N1 C1 O1 120.01(17) . . ?
N1 C1 C2 121.57(17) . . ?
O1 C1 C2 118.42(16) . . ?
C3 C2 C1 119.94(18) . . ?
C3 C2 C10 124.27(18) . . ?
C1 C2 C10 115.79(16) . . ?
C2 C3 C4 121.45(18) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C9 C4 C5 117.41(19) . . ?
C9 C4 C3 117.85(17) . . ?
C5 C4 C3 124.74(18) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 O1 117.14(17) . . ?
C8 C9 C4 121.98(18) . . ?
O1 C9 C4 120.88(17) . . ?
O2 C10 C2 109.48(17) . . ?
O2 C10 H10A 109.5(11) . . ?
C2 C10 H10A 109.7(11) . . ?
O2 C11 C12 110.0(2) . . ?
O2 C11 H11A 108.9(11) . . ?
C12 C11 H11A 109.6(11) . . ?
C11 C12 H12A 112.8(17) . . ?
C11 C12 H12B 110.3(11) . . ?
H12A C12 H12B 110.6(15) . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C14 C13 C14 118.80(18) . 4_565 ?
C14 C13 N1 120.49(9) . . ?
C14 C13 N1 120.49(9) 4_565 . ?
C13 C14 C15 120.27(15) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 121.74(16) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C15 117.17(19) 4_565 . ?
C15 C16 C17 121.41(9) 4_565 . ?
C15 C16 C17 121.41(9) . . ?
C16 C17 H17A 109.3(17) . . ?
C16 C17 H17B 113.1(12) . . ?
H17A C17 H17B 107.5(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.374(2) . ?
O1 C9 1.382(2) . ?
O2 C10 1.408(2) . ?
O2 C11 1.417(2) . ?
N1 C1 1.266(3) . ?
N1 C13 1.424(2) . ?
C1 C2 1.458(3) . ?
C2 C3 1.332(3) . ?
C2 C10 1.499(3) . ?
C3 C4 1.444(3) . ?
C3 H3 0.9300 . ?
C4 C9 1.393(3) . ?
C4 C5 1.398(3) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C7 C6 1.380(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(3) . ?
C8 H8 0.9300 . ?
C10 H10A 1.02(2) . ?
C11 C12 1.483(3) . ?
C11 H11A 0.99(2) . ?
C12 H12A 0.98(3) . ?
C12 H12B 0.97(2) . ?
C6 H6 0.9300 . ?
C13 C14 1.3780(19) . ?
C13 C14 1.3780(19) 4_565 ?
C14 C15 1.390(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9300 . ?
C16 C15 1.380(2) 4_565 ?
C16 C17 1.507(3) . ?
C17 H17A 0.95(3) . ?
C17 H17B 0.90(2) . ?
