#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:33:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178396 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/18/4021848.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_4021848
loop_
_publ_author_name
'Yugang Chen'
'Mark G. Steinmetz'
_publ_section_title
;
 Photoactivation of Amino-Substituted 1,4-Benzoquinones for Release
 of Carboxylate and Phenolate Leaving Groups Using Visible Light
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6053
_journal_page_last               6060
_journal_paper_doi               10.1021/jo060790g
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C21 H25 N O3'
_chemical_formula_weight         339.42
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.496(3)
_cell_angle_beta                 82.929(4)
_cell_angle_gamma                88.154(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6660(18)
_cell_length_b                   9.906(2)
_cell_length_c                   11.420(3)
_cell_measurement_reflns_used    2236
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2.5
_cell_volume                     848.8(3)
_computing_cell_refinement       'SAINT v7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 v2.0-2 (Bruker, 2005)'
_computing_data_reduction        'SADABS-2004/1 (Bruker, 2005)'
_computing_molecular_graphics    'XP v5.1 (Bruker, 1998)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)'
_computing_structure_solution    'XS/SHELXTL v6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       '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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13771
_diffrn_reflns_theta_full        31.99
_diffrn_reflns_theta_max         31.99
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0882P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                3388
_reflns_number_total             5387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060790gsi20060417_123531.cif
_cod_database_code               4021848
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
O1 O -0.28648(15) -0.15638(11) 0.02472(10) 0.0272(3) Uani 1 1 d
O2 O 0.17790(14) -0.00916(11) 0.30555(10) 0.0231(2) Uani 1 1 d
O3 O -0.14448(16) 0.36732(12) 0.42555(11) 0.0330(3) Uani 1 1 d
N1 N -0.04905(17) -0.30881(13) 0.06206(12) 0.0237(3) Uani 1 1 d
C1 C -0.1001(2) -0.43567(17) 0.14821(16) 0.0286(4) Uani 1 1 d
C2 C -0.2940(2) -0.45355(19) 0.14170(17) 0.0313(4) Uani 1 1 d
C3 C -0.3127(2) -0.39650(18) 0.01151(16) 0.0278(4) Uani 1 1 d
C4 C -0.1922(2) -0.27442(17) -0.01332(15) 0.0249(3) Uani 1 1 d
C5 C -0.1806(2) -0.10441(16) 0.09477(14) 0.0225(3) Uani 1 1 d
C6 C -0.2152(2) 0.01277(15) 0.14276(14) 0.0221(3) Uani 1 1 d
C7 C -0.09433(19) 0.04563(15) 0.21693(13) 0.0201(3) Uani 1 1 d
C8 C -0.1268(2) 0.16920(16) 0.27696(15) 0.0227(3) Uani 1 1 d
C9 C 0.0083(2) 0.18266(15) 0.35789(13) 0.0205(3) Uani 1 1 d
C10 C -0.0164(2) 0.29046(16) 0.43151(14) 0.0232(3) Uani 1 1 d
C11 C 0.1161(2) 0.30163(18) 0.51600(15) 0.0256(3) Uani 1 1 d
C12 C 0.3013(2) 0.25387(16) 0.47374(14) 0.0227(3) Uani 1 1 d
C13 C 0.2898(2) 0.10956(16) 0.44312(15) 0.0225(3) Uani 1 1 d
C14 C 0.1486(2) 0.09797(15) 0.36643(13) 0.0203(3) Uani 1 1 d
C15 C 0.05163(19) -0.03852(15) 0.23477(13) 0.0194(3) Uani 1 1 d
C16 C 0.0858(2) -0.15922(15) 0.18604(13) 0.0206(3) Uani 1 1 d
C17 C -0.0378(2) -0.19046(15) 0.11714(14) 0.0207(3) Uani 1 1 d
C18 C -0.3732(2) 0.1012(2) 0.1176(2) 0.0321(4) Uani 1 1 d
C19 C 0.3794(2) 0.35299(19) 0.36424(16) 0.0300(4) Uani 1 1 d
C20 C 0.4188(3) 0.2497(2) 0.57299(17) 0.0322(4) Uani 1 1 d
C21 C 0.2438(2) -0.24821(18) 0.21101(17) 0.0265(4) Uani 1 1 d
H1A H -0.070(2) -0.4233(19) 0.2271(17) 0.033(5) Uiso 1 1 d
H1B H -0.027(3) -0.520(2) 0.1227(17) 0.036(5) Uiso 1 1 d
H2A H -0.329(3) -0.551(2) 0.1614(18) 0.041(6) Uiso 1 1 d
H2B H -0.364(3) -0.389(2) 0.1914(17) 0.041(6) Uiso 1 1 d
H3A H -0.430(3) -0.3693(19) -0.0041(16) 0.035(5) Uiso 1 1 d
H3B H -0.272(2) -0.4627(19) -0.0368(16) 0.030(5) Uiso 1 1 d
H4 H -0.153(2) -0.2506(17) -0.0982(15) 0.022(4) Uiso 1 1 d
H8A H -0.131(2) 0.2535(19) 0.2159(16) 0.027(5) Uiso 1 1 d
H8B H -0.249(3) 0.1641(19) 0.3255(16) 0.033(5) Uiso 1 1 d
H11A H 0.117(2) 0.398(2) 0.5303(16) 0.033(5) Uiso 1 1 d
H11B H 0.072(3) 0.242(2) 0.5907(18) 0.036(5) Uiso 1 1 d
H13A H 0.269(2) 0.045(2) 0.5163(17) 0.034(5) Uiso 1 1 d
H13B H 0.405(3) 0.0761(18) 0.4028(16) 0.029(5) Uiso 1 1 d
H18A H -0.434(3) 0.072(2) 0.060(2) 0.065(8) Uiso 1 1 d
H18B H -0.456(3) 0.097(2) 0.185(2) 0.061(7) Uiso 1 1 d
H18C H -0.346(3) 0.194(3) 0.093(2) 0.057(7) Uiso 1 1 d
H19A H 0.314(2) 0.3554(18) 0.2933(16) 0.029(5) Uiso 1 1 d
H19B H 0.507(3) 0.328(2) 0.3384(18) 0.047(6) Uiso 1 1 d
H19C H 0.380(3) 0.449(2) 0.3795(18) 0.046(6) Uiso 1 1 d
H20A H 0.532(3) 0.213(2) 0.5522(17) 0.037(5) Uiso 1 1 d
H20B H 0.378(3) 0.187(2) 0.6445(19) 0.044(6) Uiso 1 1 d
H20C H 0.419(3) 0.343(2) 0.5959(18) 0.044(6) Uiso 1 1 d
H21A H 0.259(3) -0.322(2) 0.1661(18) 0.044(6) Uiso 1 1 d
H21B H 0.228(3) -0.293(2) 0.2923(19) 0.042(6) Uiso 1 1 d
H21C H 0.350(3) -0.196(2) 0.1951(17) 0.040(5) 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
C5 O1 C4 105.85(11)
C14 O2 C15 118.86(11)
C17 N1 C4 103.79(12)
C17 N1 C1 113.96(13)
C4 N1 C1 107.53(13)
N1 C1 C2 105.48(13)
C1 C2 C3 102.69(14)
C4 C3 C2 102.45(14)
O1 C4 N1 107.49(12)
O1 C4 C3 109.58(14)
N1 C4 C3 106.59(13)
C6 C5 O1 124.90(13)
C6 C5 C17 123.71(13)
O1 C5 C17 111.29(13)
C5 C6 C7 116.32(13)
C5 C6 C18 121.74(14)
C7 C6 C18 121.94(14)
C15 C7 C6 119.35(13)
C15 C7 C8 121.05(13)
C6 C7 C8 119.59(13)
C9 C8 C7 112.05(12)
C14 C9 C10 119.47(14)
C14 C9 C8 122.43(14)
C10 C9 C8 118.09(13)
O3 C10 C9 120.15(14)
O3 C10 C11 121.54(14)
C9 C10 C11 118.30(13)
C10 C11 C12 114.10(13)
C20 C12 C11 109.91(14)
C20 C12 C19 108.87(14)
C11 C12 C19 109.76(14)
C20 C12 C13 109.31(13)
C11 C12 C13 108.42(13)
C19 C12 C13 110.56(14)
C14 C13 C12 112.76(12)
C9 C14 O2 123.53(13)
C9 C14 C13 124.51(14)
O2 C14 C13 111.96(12)
C7 C15 O2 121.75(13)
C7 C15 C16 124.09(13)
O2 C15 C16 114.16(12)
C17 C16 C15 114.99(13)
C17 C16 C21 123.27(14)
C15 C16 C21 121.72(13)
C16 C17 C5 121.46(14)
C16 C17 N1 129.15(13)
C5 C17 N1 109.36(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.3735(17)
O1 C4 1.4539(19)
O2 C14 1.3601(17)
O2 C15 1.4012(17)
O3 C10 1.2244(19)
N1 C17 1.4286(19)
N1 C4 1.474(2)
N1 C1 1.493(2)
C1 C2 1.515(3)
C2 C3 1.523(3)
C3 C4 1.513(2)
C5 C6 1.368(2)
C5 C17 1.388(2)
C6 C7 1.409(2)
C6 C18 1.501(2)
C7 C15 1.389(2)
C7 C8 1.498(2)
C8 C9 1.493(2)
C9 C14 1.346(2)
C9 C10 1.459(2)
C10 C11 1.503(2)
C11 C12 1.528(2)
C12 C20 1.527(2)
C12 C19 1.528(2)
C12 C13 1.534(2)
C13 C14 1.492(2)
C15 C16 1.404(2)
C16 C17 1.377(2)
C16 C21 1.503(2)
