#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:29:08 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178480 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/01/4030164.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_4030164
loop_
_publ_author_name
'Helmy, Sameh'
'Oh, Saemi'
'Leibfarth, Frank A.'
'Hawker, Craig J.'
'Read de Alaniz, Javier'
_publ_section_title
;
 Design and synthesis of donor-acceptor Stenhouse adducts: a visible light
 photoswitch derived from furfural.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11316
_journal_page_last               11329
_journal_paper_doi               10.1021/jo502206g
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C21 H25 N O6'
_chemical_formula_weight         387.42
_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                 101.320(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.287(8)
_cell_length_b                   10.538(7)
_cell_length_c                   14.009(10)
_cell_measurement_temperature    100(2)
_cell_volume                     1923(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'bruker kappa apex'
_diffrn_measurement_method       'omega scan'
_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  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11892
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.646
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.646
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                3855
_reflns_number_total             4752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            18.cif
_cod_data_source_block           s08312011_01
_cod_depositor_comments
'Adding full bibliography for 4030156--4030166.cif.'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4030164
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
C1 C 1.21175(8) 0.33917(10) -0.01925(8) 0.0176(2) Uani 1 1 d .
C2 C 1.20650(8) 0.42876(11) 0.13760(8) 0.0162(2) Uani 1 1 d .
C3 C 1.12244(7) 0.34416(10) 0.14271(8) 0.0156(2) Uani 1 1 d .
C4 C 1.10907(8) 0.23652(11) 0.08119(8) 0.0155(2) Uani 1 1 d .
C5 C 1.13084(9) 0.41959(11) -0.08199(9) 0.0224(3) Uani 1 1 d .
H5A H 1.0774 0.4412 -0.0455 0.034 Uiso 1 1 calc R
H5B H 1.1003 0.3722 -0.1407 0.034 Uiso 1 1 calc R
H5C H 1.1623 0.4976 -0.1005 0.034 Uiso 1 1 calc R
C6 C 1.29582(9) 0.29629(12) -0.06970(9) 0.0230(3) Uani 1 1 d .
H6A H 1.3317 0.3706 -0.0887 0.035 Uiso 1 1 calc R
H6B H 1.2661 0.2473 -0.1279 0.035 Uiso 1 1 calc R
H6C H 1.3445 0.2430 -0.0254 0.035 Uiso 1 1 calc R
C7 C 1.06796(8) 0.36881(11) 0.21909(8) 0.0159(2) Uani 1 1 d .
H7 H 1.0924 0.4413 0.2569 0.019 Uiso 1 1 calc R
C8 C 0.98766(8) 0.30949(11) 0.24922(8) 0.0168(2) Uani 1 1 d .
C9 C 0.95276(8) 0.35550(11) 0.33164(8) 0.0176(2) Uani 1 1 d .
H9 H 0.9855 0.4291 0.3623 0.021 Uiso 1 1 calc R
C10 C 0.87582(8) 0.30317(11) 0.37123(8) 0.0175(2) Uani 1 1 d .
H10 H 0.8443 0.2256 0.3471 0.021 Uiso 1 1 calc R
C11 C 0.84496(8) 0.36753(11) 0.44843(8) 0.0174(2) Uani 1 1 d .
H11 H 0.8845 0.4399 0.4724 0.021 Uiso 1 1 calc R
C12 C 0.74476(8) 0.41951(11) 0.57097(8) 0.0197(2) Uani 1 1 d .
H12A H 0.7877 0.4970 0.5779 0.024 Uiso 1 1 calc R
H12B H 0.7608 0.3719 0.6330 0.024 Uiso 1 1 calc R
C13 C 0.63240(8) 0.45620(11) 0.54975(9) 0.0194(2) Uani 1 1 d .
H13A H 0.6163 0.5044 0.6055 0.023 Uiso 1 1 calc R
H13B H 0.6182 0.5117 0.4916 0.023 Uiso 1 1 calc R
C14 C 0.58935(8) 0.27943(12) 0.45088(9) 0.0231(3) Uani 1 1 d .
H14A H 0.5760 0.3358 0.3932 0.028 Uiso 1 1 calc R
H14B H 0.5422 0.2060 0.4374 0.028 Uiso 1 1 calc R
C15 C 0.69921(8) 0.23273(11) 0.46712(9) 0.0215(3) Uani 1 1 d .
H15A H 0.7113 0.1699 0.5207 0.026 Uiso 1 1 calc R
H15B H 0.7121 0.1909 0.4074 0.026 Uiso 1 1 calc R
C16 C 0.42737(9) -0.09235(11) 0.31981(8) 0.0213(3) Uani 1 1 d .
H16 H 0.4426 -0.1642 0.3611 0.026 Uiso 1 1 calc R
C17 C 0.50554(9) -0.01372(12) 0.30391(9) 0.0242(3) Uani 1 1 d .
H17 H 0.5746 -0.0321 0.3337 0.029 Uiso 1 1 calc R
C18 C 0.48366(10) 0.09112(12) 0.24503(9) 0.0264(3) Uani 1 1 d .
H18 H 0.5375 0.1450 0.2340 0.032 Uiso 1 1 calc R
C19 C 0.38378(10) 0.11788(12) 0.20216(8) 0.0271(3) Uani 1 1 d .
H19 H 0.3685 0.1908 0.1621 0.033 Uiso 1 1 calc R
C20 C 0.30568(9) 0.03868(12) 0.21734(8) 0.0242(3) Uani 1 1 d .
H20 H 0.2367 0.0569 0.1873 0.029 Uiso 1 1 calc R
C21 C 0.32754(9) -0.06672(12) 0.27591(8) 0.0214(3) Uani 1 1 d .
H21 H 0.2738 -0.1215 0.2859 0.026 Uiso 1 1 calc R
N N 0.76862(6) 0.34068(9) 0.49174(7) 0.0168(2) Uani 1 1 d .
O1 O 1.23762(6) 0.51302(8) 0.19479(6) 0.02141(19) Uani 1 1 d .
O2 O 1.05298(6) 0.14402(7) 0.08675(6) 0.02017(18) Uani 1 1 d .
O3 O 1.25996(5) 0.40937(7) 0.06420(5) 0.01723(18) Uani 1 1 d .
O4 O 1.16674(6) 0.22623(7) 0.01107(6) 0.01834(18) Uani 1 1 d .
O7 O 0.93672(6) 0.20673(9) 0.20609(6) 0.0280(2) Uani 1 1 d .
H7A H 0.9686 0.1765 0.1651 0.042 Uiso 1 1 calc R
O8 O 0.56924(6) 0.34660(8) 0.53308(6) 0.02080(19) 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
O3 C1 O4 109.54(9)
O3 C1 C6 106.61(9)
O4 C1 C6 106.34(10)
O3 C1 C5 109.92(10)
O4 C1 C5 110.36(10)
C6 C1 C5 113.90(11)
O1 C2 O3 116.33(10)
O1 C2 C3 125.94(11)
O3 C2 C3 117.66(10)
C4 C3 C7 125.50(10)
C4 C3 C2 118.13(10)
C7 C3 C2 115.86(10)
O2 C4 O4 114.38(10)
O2 C4 C3 126.72(11)
O4 C4 C3 118.79(10)
C1 C5 H5A 109.5
C1 C5 H5B 109.5
H5A C5 H5B 109.5
C1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C1 C6 H6A 109.5
C1 C6 H6B 109.5
H6A C6 H6B 109.5
C1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C3 133.34(11)
C8 C7 H7 113.3
C3 C7 H7 113.3
O7 C8 C7 125.26(11)
O7 C8 C9 115.07(10)
C7 C8 C9 119.67(10)
C10 C9 C8 125.69(11)
C10 C9 H9 117.2
C8 C9 H9 117.2
C9 C10 C11 118.10(11)
C9 C10 H10 120.9
C11 C10 H10 120.9
N C11 C10 128.44(11)
N C11 H11 115.8
C10 C11 H11 115.8
N C12 C13 110.28(9)
N C12 H12A 109.6
C13 C12 H12A 109.6
N C12 H12B 109.6
C13 C12 H12B 109.6
H12A C12 H12B 108.1
O8 C13 C12 110.66(10)
O8 C13 H13A 109.5
C12 C13 H13A 109.5
O8 C13 H13B 109.5
C12 C13 H13B 109.5
H13A C13 H13B 108.1
O8 C14 C15 111.66(10)
O8 C14 H14A 109.3
C15 C14 H14A 109.3
O8 C14 H14B 109.3
C15 C14 H14B 109.3
H14A C14 H14B 107.9
N C15 C14 109.10(10)
N C15 H15A 109.9
C14 C15 H15A 109.9
N C15 H15B 109.9
C14 C15 H15B 109.9
H15A C15 H15B 108.3
C21 C16 C17 120.01(11)
C21 C16 H16 120.0
C17 C16 H16 120.0
C18 C17 C16 120.12(11)
C18 C17 H17 119.9
C16 C17 H17 119.9
C19 C18 C17 119.96(12)
C19 C18 H18 120.0
C17 C18 H18 120.0
C18 C19 C20 119.95(12)
C18 C19 H19 120.0
C20 C19 H19 120.0
C21 C20 C19 120.15(11)
C21 C20 H20 119.9
C19 C20 H20 119.9
C16 C21 C20 119.80(11)
C16 C21 H21 120.1
C20 C21 H21 120.1
C11 N C15 124.62(10)
C11 N C12 121.91(10)
C15 N C12 113.47(9)
C2 O3 C1 118.41(9)
C4 O4 C1 118.27(9)
C8 O7 H7A 109.5
C13 O8 C14 109.83(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O3 1.4248(14)
C1 O4 1.4333(15)
C1 C6 1.5039(18)
C1 C5 1.5085(16)
C2 O1 1.2130(14)
C2 O3 1.3749(15)
C2 C3 1.4418(16)
C3 C4 1.4144(17)
C3 C7 1.4285(17)
C4 O2 1.2387(14)
C4 O4 1.3635(15)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.3727(17)
C7 H7 0.9500
C8 O7 1.3547(14)
C8 C9 1.4118(18)
C9 C10 1.3709(17)
C9 H9 0.9500
C10 C11 1.4042(17)
C10 H10 0.9500
C11 N 1.3110(16)
C11 H11 0.9500
C12 N 1.4698(16)
C12 C13 1.5141(17)
C12 H12A 0.9900
C12 H12B 0.9900
C13 O8 1.4198(15)
C13 H13A 0.9900
C13 H13B 0.9900
C14 O8 1.4210(16)
C14 C15 1.5148(18)
C14 H14A 0.9900
C14 H14B 0.9900
C15 N 1.4624(16)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C21 1.3750(17)
C16 C17 1.3805(18)
C16 H16 0.9500
C17 C18 1.3752(19)
C17 H17 0.9500
C18 C19 1.3742(19)
C18 H18 0.9500
C19 C20 1.3804(19)
C19 H19 0.9500
C20 C21 1.3775(18)
C20 H20 0.9500
C21 H21 0.9500
O7 H7A 0.8400
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
O1 C2 C3 C4 -168.04(10)
O3 C2 C3 C4 8.68(14)
O1 C2 C3 C7 4.22(16)
O3 C2 C3 C7 -179.07(9)
C7 C3 C4 O2 -4.24(17)
C2 C3 C4 O2 167.19(10)
C7 C3 C4 O4 179.85(9)
C2 C3 C4 O4 -8.72(14)
C4 C3 C7 C8 -6.22(18)
C2 C3 C7 C8 -177.82(11)
C3 C7 C8 O7 -2.22(19)
C3 C7 C8 C9 177.55(11)
O7 C8 C9 C10 1.95(16)
C7 C8 C9 C10 -177.84(10)
C8 C9 C10 C11 -174.65(10)
C9 C10 C11 N 174.19(10)
N C12 C13 O8 55.43(12)
O8 C14 C15 N -56.15(13)
C21 C16 C17 C18 0.72(18)
C16 C17 C18 C19 0.18(18)
C17 C18 C19 C20 -0.76(18)
C18 C19 C20 C21 0.44(18)
C17 C16 C21 C20 -1.03(18)
C19 C20 C21 C16 0.46(18)
C10 C11 N C15 0.84(17)
C10 C11 N C12 -178.76(10)
C14 C15 N C11 -128.57(11)
C14 C15 N C12 51.06(12)
C13 C12 N C11 128.30(11)
C13 C12 N C15 -51.34(12)
O1 C2 O3 C1 -162.31(9)
C3 C2 O3 C1 20.66(13)
O4 C1 O3 C2 -47.11(12)
C6 C1 O3 C2 -161.78(9)
C5 C1 O3 C2 74.32(12)
O2 C4 O4 C1 163.15(9)
C3 C4 O4 C1 -20.45(13)
O3 C1 O4 C4 47.09(12)
C6 C1 O4 C4 161.93(8)
C5 C1 O4 C4 -74.07(12)
C12 C13 O8 C14 -61.29(12)
C15 C14 O8 C13 62.27(12)
