#------------------------------------------------------------------------------
#$Date: 2017-11-06 01:05:18 +0200 (Mon, 06 Nov 2017) $
#$Revision: 202604 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/30/4033047.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_4033047
loop_
_publ_author_name
'Zhao, Qinglan'
'Xiang, Haoyue'
'Xiao, Jun-An'
'Xia, Peng-Ju'
'Wang, Jun-Jie'
'Chen, Xiaoqing'
'Yang, Hua'
_publ_section_title
;
 Selectfluor-Triggered Tandem Cyclization of o-Hydroxyarylenaminones To
 Access Difluorinated 2-Amino-Substituted Chromanones.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9837
_journal_page_last               9843
_journal_paper_doi               10.1021/acs.joc.7b01339
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C44 H44 F8 N4 O8'
_chemical_formula_weight         908.83
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.577(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            1
_cell_length_a                   8.3051(4)
_cell_length_b                   10.1444(5)
_cell_length_c                   12.8453(5)
_cell_measurement_reflns_used    1979
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.45
_cell_volume                     1081.81(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6287
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.119
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0363
_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)+(0.0481P)²+0.2225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                1566
_reflns_number_total             1979
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01339_si_002.cif
_cod_data_source_block           yangh133_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4033047
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O2 O 0.33937(12) 0.73173(11) 0.41275(9) 0.0579(3) Uani 1 1 d .
F2 F -0.09090(12) 0.72799(12) 0.42896(11) 0.0918(4) Uani 1 1 d .
F1 F 0.05415(15) 0.75116(11) 0.29206(9) 0.0867(4) Uani 1 1 d .
O1 O -0.03870(14) 0.47976(13) 0.37476(11) 0.0756(4) Uani 1 1 d .
N1 N 0.17004(18) 0.89452(14) 0.48338(11) 0.0636(4) Uani 1 1 d .
C4 C 0.36714(17) 0.60441(15) 0.38545(11) 0.0480(4) Uani 1 1 d .
C9 C 0.18527(18) 0.75998(15) 0.46003(13) 0.0539(4) Uani 1 1 d .
H9 H 0.1844 0.7122 0.5263 0.065 Uiso 1 1 calc R
C5 C 0.24414(18) 0.51240(15) 0.37088(11) 0.0488(4) Uani 1 1 d .
C3 C 0.52643(19) 0.56741(18) 0.37098(12) 0.0583(4) Uani 1 1 d .
H3 H 0.6092 0.6282 0.3809 0.070 Uiso 1 1 calc R
C7 C 0.07677(19) 0.55273(17) 0.37935(12) 0.0545(4) Uani 1 1 d .
C8 C 0.05418(19) 0.70106(18) 0.39112(13) 0.0593(4) Uani 1 1 d .
C6 C 0.2831(2) 0.38308(18) 0.34349(14) 0.0644(5) Uani 1 1 d .
H6 H 0.2019 0.3205 0.3352 0.077 Uiso 1 1 calc R
C2 C 0.5600(2) 0.4409(2) 0.34201(13) 0.0674(5) Uani 1 1 d .
H2 H 0.6662 0.4168 0.3309 0.081 Uiso 1 1 calc R
C1 C 0.4395(2) 0.3481(2) 0.32888(15) 0.0732(5) Uani 1 1 d .
H1 H 0.4649 0.2621 0.3102 0.088 Uiso 1 1 calc R
C10 C 0.1902(3) 0.98864(19) 0.39924(17) 0.0856(6) Uani 1 1 d .
H10A H 0.3010 0.9901 0.3798 0.128 Uiso 1 1 calc R
H10B H 0.1591 1.0748 0.4221 0.128 Uiso 1 1 calc R
H10C H 0.1238 0.9631 0.3403 0.128 Uiso 1 1 calc R
C11 C 0.2578(3) 0.9340(2) 0.57753(17) 0.0914(7) Uani 1 1 d .
H11A H 0.2360 0.8729 0.6324 0.137 Uiso 1 1 calc R
H11B H 0.2242 1.0208 0.5975 0.137 Uiso 1 1 calc R
H11C H 0.3712 0.9346 0.5649 0.137 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'
F F 0.0171 0.0103 '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
C4 O2 C9 116.79(11)
C9 N1 C11 113.61(15)
C9 N1 C10 117.79(14)
C11 N1 C10 111.87(17)
O2 C4 C3 117.33(14)
O2 C4 C5 122.84(13)
C3 C4 C5 119.83(15)
N1 C9 O2 111.40(13)
N1 C9 C8 116.30(14)
O2 C9 C8 107.76(13)
N1 C9 H9 107.0
O2 C9 H9 107.0
C8 C9 H9 107.0
C4 C5 C6 119.25(14)
C4 C5 C7 119.99(14)
C6 C5 C7 120.69(15)
C2 C3 C4 119.40(16)
C2 C3 H3 120.3
C4 C3 H3 120.3
O1 C7 C5 125.50(16)
O1 C7 C8 120.56(15)
C5 C7 C8 113.90(14)
F2 C8 F1 106.50(14)
F2 C8 C9 110.38(14)
F1 C8 C9 112.32(14)
F2 C8 C7 110.59(14)
F1 C8 C7 105.71(14)
C9 C8 C7 111.15(14)
C1 C6 C5 120.43(17)
C1 C6 H6 119.8
C5 C6 H6 119.8
C3 C2 C1 121.41(16)
C3 C2 H2 119.3
C1 C2 H2 119.3
C6 C1 C2 119.66(17)
C6 C1 H1 120.2
C2 C1 H1 120.2
N1 C10 H10A 109.5
N1 C10 H10B 109.5
H10A C10 H10B 109.5
N1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N1 C11 H11A 109.5
N1 C11 H11B 109.5
H11A C11 H11B 109.5
N1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C4 1.3597(18)
O2 C9 1.4599(18)
F2 C8 1.3398(18)
F1 C8 1.370(2)
O1 C7 1.2116(19)
N1 C9 1.404(2)
N1 C11 1.451(3)
N1 C10 1.455(2)
C4 C3 1.393(2)
C4 C5 1.393(2)
C9 C8 1.508(2)
C9 H9 0.9800
C5 C6 1.398(2)
C5 C7 1.456(2)
C3 C2 1.367(3)
C3 H3 0.9300
C7 C8 1.524(2)
C6 C1 1.365(3)
C6 H6 0.9300
C2 C1 1.381(3)
C2 H2 0.9300
C1 H1 0.9300
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
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
C9 O2 C4 C3 -160.68(13)
C9 O2 C4 C5 19.9(2)
C11 N1 C9 O2 -78.43(18)
C10 N1 C9 O2 55.2(2)
C11 N1 C9 C8 157.57(16)
C10 N1 C9 C8 -68.8(2)
C4 O2 C9 N1 -179.21(13)
C4 O2 C9 C8 -50.51(17)
O2 C4 C5 C6 -179.57(14)
C3 C4 C5 C6 1.1(2)
O2 C4 C5 C7 3.3(2)
C3 C4 C5 C7 -176.04(13)
O2 C4 C3 C2 -179.06(14)
C5 C4 C3 C2 0.3(2)
C4 C5 C7 O1 -175.04(15)
C6 C5 C7 O1 7.9(3)
C4 C5 C7 C8 7.1(2)
C6 C5 C7 C8 -169.93(14)
N1 C9 C8 F2 -52.0(2)
O2 C9 C8 F2 -177.86(13)
N1 C9 C8 F1 66.69(18)
O2 C9 C8 F1 -59.17(17)
N1 C9 C8 C7 -175.09(13)
O2 C9 C8 C7 59.05(17)
O1 C7 C8 F2 20.5(2)
C5 C7 C8 F2 -161.57(13)
O1 C7 C8 F1 -94.41(18)
C5 C7 C8 F1 83.54(16)
O1 C7 C8 C9 143.46(16)
C5 C7 C8 C9 -38.60(19)
C4 C5 C6 C1 -1.5(2)
C7 C5 C6 C1 175.61(16)
C4 C3 C2 C1 -1.4(3)
C5 C6 C1 C2 0.5(3)
C3 C2 C1 C6 1.0(3)
