#------------------------------------------------------------------------------
#$Date: 2019-11-23 23:59:40 +0100 (Sat 23 de Nov de 2019) $
#$Revision: 235881 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/72/4037270.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_4037270
loop_
_publ_author_name
'Baker, Matthew B.'
'Ferreira, Renan B.'
'Tasseroul, Jonathan'
'Lampkins, Andrew J.'
'Al Abbas, Alexandre'
'Abboud, Khalil A.'
'Castellano, Ronald K.'
_publ_section_title
;
 Selective and Sequential Aminolysis of Benzotrifuranone: Synergism of
 Electronic Effects and Ring Strain Gradient.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9279
_journal_page_last               9288
_journal_paper_doi               10.1021/acs.joc.6b01867
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C17 H13 N O7, 0.5(C6 H6)'
_chemical_formula_sum            'C20 H16 N O7'
_chemical_formula_weight         382.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-06-30 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 100.698(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.2630(7)
_cell_length_b                   4.8365(2)
_cell_length_c                   19.3532(7)
_cell_measurement_reflns_used    9826
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.
_cell_measurement_theta_min      2.
_cell_volume                     1679.74(11)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2008)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2008)'
_computing_data_reduction        'Bruker Apex2 SAINT (Bruker, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16071
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         1.699
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9820
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL2014 (Sheldrick, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       needle
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0829P)²+0.4568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3028
_reflns_number_total             3866
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b01867_si_002.cif
_cod_data_source_block           1c
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4037270
_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   0.968
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.77878(6) 1.3442(2) 0.52602(6) 0.0176(3) Uani 1 1 d . .
O2 O 0.76387(7) 1.6299(3) 0.43321(6) 0.0242(3) Uani 1 1 d . .
O3 O 0.73846(6) 0.6229(2) 0.68075(5) 0.0161(3) Uani 1 1 d . .
O4 O 0.84941(6) 0.5898(3) 0.75246(6) 0.0221(3) Uani 1 1 d . .
O5 O 0.55569(6) 0.8231(3) 0.47656(6) 0.0173(3) Uani 1 1 d . .
H5 H 0.5405(14) 0.934(6) 0.4440(13) 0.041(7) Uiso 1 1 d . .
O6 O 0.50649(6) 0.8809(2) 0.63257(6) 0.0186(3) Uani 1 1 d . .
O7 O 0.36398(7) 0.3147(3) 0.70259(7) 0.0307(3) Uani 1 1 d . .
N1 N 0.52200(8) 0.4982(3) 0.69976(7) 0.0199(3) Uani 1 1 d . .
H1 H 0.5421(12) 0.346(5) 0.7076(11) 0.028(6) Uiso 1 1 d . .
C1 C 0.73885(9) 1.4460(4) 0.46261(8) 0.0185(3) Uani 1 1 d . .
C2 C 0.66593(9) 1.2870(4) 0.44282(8) 0.0173(3) Uani 1 1 d . .
H2A H 0.6224 1.4123 0.4384 0.021 Uiso 1 1 calc R U
H2B H 0.6638 1.1847 0.3982 0.021 Uiso 1 1 calc R U
C3 C 0.66887(8) 1.0931(3) 0.50363(8) 0.0148(3) Uani 1 1 d . .
C4 C 0.73666(8) 1.1361(3) 0.54890(8) 0.0150(3) Uani 1 1 d . .
C5 C 0.81052(9) 0.7100(4) 0.70518(8) 0.0173(3) Uani 1 1 d . .
C6 C 0.82836(8) 0.9583(4) 0.66336(8) 0.0179(3) Uani 1 1 d . .
H6A H 0.8362 1.1267 0.6929 0.022 Uiso 1 1 calc R U
H6B H 0.8730 0.9249 0.6422 0.022 Uiso 1 1 calc R U
C7 C 0.75945(8) 0.9802(3) 0.60833(8) 0.0155(3) Uani 1 1 d . .
C8 C 0.70888(8) 0.7812(3) 0.62139(8) 0.0144(3) Uani 1 1 d . .
C9 C 0.53500(8) 0.6499(3) 0.64592(8) 0.0150(3) Uani 1 1 d . .
C10 C 0.58684(8) 0.5195(3) 0.60184(8) 0.0149(3) Uani 1 1 d . .
H10A H 0.6158 0.3695 0.6291 0.018 Uiso 1 1 calc R U
H10B H 0.5568 0.4369 0.5590 0.018 Uiso 1 1 calc R U
C11 C 0.63969(8) 0.7295(3) 0.58107(8) 0.0140(3) Uani 1 1 d . .
C12 C 0.62072(8) 0.8897(3) 0.51913(8) 0.0138(3) Uani 1 1 d . .
C13 C 0.47291(10) 0.5939(4) 0.74666(9) 0.0238(4) Uani 1 1 d . .
H13A H 0.4460 0.7611 0.7261 0.029 Uiso 1 1 calc R U
H13B H 0.5037 0.6468 0.7924 0.029 Uiso 1 1 calc R U
C14 C 0.41797(10) 0.3842(4) 0.75886(9) 0.0249(4) Uani 1 1 d . .
C15 C 0.40664(12) 0.2455(5) 0.8164(1) 0.0330(5) Uani 1 1 d . .
H15 H 0.4363 0.2562 0.8622 0.040 Uiso 1 1 calc R U
C16 C 0.34178(12) 0.0800(5) 0.79564(11) 0.0367(5) Uani 1 1 d . .
H16 H 0.3197 -0.0401 0.8248 0.044 Uiso 1 1 calc R U
C17 C 0.31809(10) 0.1271(5) 0.72689(11) 0.0329(5) Uani 1 1 d . .
H17 H 0.2757 0.0431 0.6989 0.039 Uiso 1 1 calc R U
C18 C 0.95982(14) 0.7942(6) 0.46314(14) 0.0511(6) Uani 1 1 d . .
H18 H 0.9322 0.6491 0.4373 0.061 Uiso 1 1 calc R U
C19 C 0.92503(13) 0.9691(6) 0.50209(13) 0.0497(7) Uani 1 1 d . .
H19 H 0.8735 0.9472 0.5031 0.060 Uiso 1 1 calc R U
C20 C 0.96490(14) 1.1746(6) 0.53932(13) 0.0513(7) Uani 1 1 d . .
H20 H 0.9415 1.2968 0.5670 0.062 Uiso 1 1 calc R U
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
C4 O1 C1 107.82(12) . .
C5 O3 C8 108.19(12) . .
C12 O5 H5 116.1(18) . .
C14 O7 C17 106.53(15) . .
C9 N1 C13 121.96(15) . .
C9 N1 H1 119.9(15) . .
C13 N1 H1 118.1(15) . .
O2 C1 O1 119.94(15) . .
O2 C1 C2 130.63(15) . .
O1 C1 C2 109.43(13) . .
C3 C2 C1 102.49(13) . .
C3 C2 H2A 111.3 . .
C1 C2 H2A 111.3 . .
C3 C2 H2B 111.3 . .
C1 C2 H2B 111.3 . .
H2A C2 H2B 109.2 . .
C12 C3 C4 119.61(14) . .
C12 C3 C2 132.95(14) . .
C4 C3 C2 107.38(13) . .
C7 C4 O1 124.43(14) . .
C7 C4 C3 122.71(15) . .
O1 C4 C3 112.83(13) . .
O4 C5 O3 120.39(15) . .
O4 C5 C6 129.45(15) . .
O3 C5 C6 110.16(13) . .
C7 C6 C5 101.56(13) . .
C7 C6 H6A 111.5 . .
C5 C6 H6A 111.5 . .
C7 C6 H6B 111.5 . .
C5 C6 H6B 111.5 . .
H6A C6 H6B 109.3 . .
C4 C7 C8 115.11(14) . .
C4 C7 C6 136.05(15) . .
C8 C7 C6 108.77(13) . .
C11 C8 C7 126.36(14) . .
C11 C8 O3 122.53(14) . .
C7 C8 O3 111.05(13) . .
O6 C9 N1 122.08(15) . .
O6 C9 C10 122.50(14) . .
N1 C9 C10 115.43(14) . .
C11 C10 C9 111.45(13) . .
C11 C10 H10A 109.3 . .
C9 C10 H10A 109.3 . .
C11 C10 H10B 109.3 . .
C9 C10 H10B 109.3 . .
H10A C10 H10B 108.0 . .
C8 C11 C12 115.75(14) . .
C8 C11 C10 122.44(14) . .
C12 C11 C10 121.80(13) . .
O5 C12 C3 123.82(14) . .
O5 C12 C11 115.77(14) . .
C3 C12 C11 120.37(14) . .
N1 C13 C14 113.22(15) . .
N1 C13 H13A 108.9 . .
C14 C13 H13A 108.9 . .
N1 C13 H13B 108.9 . .
C14 C13 H13B 108.9 . .
H13A C13 H13B 107.7 . .
C15 C14 O7 109.67(17) . .
C15 C14 C13 133.39(18) . .
O7 C14 C13 116.88(15) . .
C14 C15 C16 107.08(18) . .
C14 C15 H15 126.5 . .
C16 C15 H15 126.5 . .
C17 C16 C15 106.42(18) . .
C17 C16 H16 126.8 . .
C15 C16 H16 126.8 . .
C16 C17 O7 110.29(18) . .
C16 C17 H17 124.9 . .
O7 C17 H17 124.9 . .
C19 C18 C20 121.0(3) . 3_776
C19 C18 H18 119.5 . .
C20 C18 H18 119.5 3_776 .
C20 C19 C18 119.2(2) . .
C20 C19 H19 120.4 . .
C18 C19 H19 120.4 . .
C19 C20 C18 119.8(2) . 3_776
C19 C20 H20 120.1 . .
C18 C20 H20 120.1 3_776 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.3881(19) .
O1 C1 1.3956(19) .
O2 C1 1.192(2) .
O3 C5 1.3789(19) .
O3 C8 1.4024(18) .
O4 C5 1.199(2) .
O5 C12 1.3526(18) .
O5 H5 0.83(3) .
O6 C9 1.239(2) .
O7 C14 1.368(2) .
O7 C17 1.376(2) .
N1 C9 1.331(2) .
N1 C13 1.464(2) .
N1 H1 0.82(2) .
C1 C2 1.524(2) .
C2 C3 1.498(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C12 1.389(2) .
C3 C4 1.393(2) .
C4 C7 1.374(2) .
C5 C6 1.517(2) .
C6 C7 1.494(2) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.389(2) .
C8 C11 1.379(2) .
C9 C10 1.524(2) .
C10 C11 1.506(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.415(2) .
C13 C14 1.476(3) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.349(3) .
C15 C16 1.424(3) .
C15 H15 0.9500 .
C16 C17 1.340(3) .
C16 H16 0.9500 .
C17 H17 0.9500 .
C18 C19 1.366(4) .
C18 C20 1.393(3) 3_776
C18 H18 0.9500 .
C19 C20 1.358(4) .
C19 H19 0.9500 .
C20 C18 1.393(3) 3_776
C20 H20 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O6 0.83(3) 1.81(3) 2.6285(17) 168(3) 3_676
N1 H1 O4 0.82(2) 2.34(2) 3.0767(19) 149(2) 2_646
