#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:43:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180312 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/26/7152630.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_7152630
loop_
_publ_author_name
'Lari, Alberth'
'Pitak, Matuesz B.'
'Coles, Simon J.'
'Rees, Gregory J.'
'Day, Stephen P.'
'Smith, Mark E.'
'Hanna, John V.'
'Wallis, John D.'
_publ_section_title
;
 Models for incomplete nucleophilic attack on a protonated carbonyl group
 and electron-deficient alkenes: salts and zwitterions from
 1-dimethylamino-naphthalene-8-carbaldehyde.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7763
_journal_page_last               7779
_journal_paper_doi               10.1039/c2ob25929j
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C19 H19 N3 O3'
_chemical_formula_sum            'C19 H19 N3 O3'
_chemical_formula_weight         337.37
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.456(3)
_cell_angle_beta                 85.190(2)
_cell_angle_gamma                65.248(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3360(4)
_cell_length_b                   8.7036(3)
_cell_length_c                   12.1220(6)
_cell_measurement_reflns_used    19881
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     795.56(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker-Nonius Roper CCD camera on κ-goniostat
;
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16118
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0489
_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)+(0.0736P)²+0.1386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1350
_reflns_number_gt                2967
_reflns_number_total             3656
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25929j.txt
_cod_data_source_block           compound_12
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7152630
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
_atom_site_refinement_flags
O1 O 1.26715(14) 0.03266(13) 0.19876(9) 0.0218(3) Uani 1 1 d .
O2 O 0.73167(14) 0.24432(13) 0.05345(8) 0.0216(3) Uani 1 1 d .
O3 O 0.88786(14) -0.24745(13) 0.23948(9) 0.0235(3) Uani 1 1 d .
N1 N 1.36070(16) -0.41177(14) 0.24705(9) 0.0171(3) Uani 1 1 d .
N2 N 1.00091(16) 0.13595(14) 0.12375(10) 0.0168(3) Uani 1 1 d .
N3 N 0.81517(15) -0.00592(15) 0.14194(10) 0.0172(3) Uani 1 1 d .
C1 C 1.40165(19) -0.53018(18) 0.34039(12) 0.0176(3) Uani 1 1 d .
C2 C 1.5311(2) -0.69053(19) 0.34403(12) 0.0226(3) Uani 1 1 d .
H2 H 1.6218 -0.7381 0.2853 0.027 Uiso 1 1 calc R
C3 C 1.5233(2) -0.78320(19) 0.44046(13) 0.0242(3) Uani 1 1 d .
H3 H 1.6117 -0.8952 0.4456 0.029 Uiso 1 1 calc R
C4 C 1.3931(2) -0.71716(18) 0.52631(12) 0.0225(3) Uani 1 1 d .
H4 H 1.3913 -0.7848 0.5880 0.027 Uiso 1 1 calc R
C5 C 1.1176(2) -0.45971(19) 0.60354(12) 0.0208(3) Uani 1 1 d .
H5 H 1.1037 -0.5128 0.6703 0.025 Uiso 1 1 calc R
C6 C 0.9987(2) -0.29711(19) 0.58464(12) 0.0207(3) Uani 1 1 d .
H6 H 0.9034 -0.2402 0.6392 0.025 Uiso 1 1 calc R
C7 C 1.01306(19) -0.21083(18) 0.48643(12) 0.0189(3) Uani 1 1 d .
H7 H 0.9290 -0.0986 0.4756 0.023 Uiso 1 1 calc R
C8 C 1.15039(19) -0.29310(17) 0.40810(11) 0.0169(3) Uani 1 1 d .
C9 C 1.27059(19) -0.45881(18) 0.42761(11) 0.0172(3) Uani 1 1 d .
C10 C 1.2608(2) -0.54799(18) 0.52340(11) 0.0187(3) Uani 1 1 d .
C11 C 1.2830(2) -0.47792(18) 0.16151(12) 0.0211(3) Uani 1 1 d .
H11A H 1.3707 -0.5892 0.1333 0.032 Uiso 1 1 calc R
H11B H 1.2506 -0.3994 0.1003 0.032 Uiso 1 1 calc R
H11C H 1.1771 -0.4884 0.1952 0.032 Uiso 1 1 calc R
C12 C 1.5164(2) -0.38782(19) 0.19307(13) 0.0221(3) Uani 1 1 d .
H12A H 1.5752 -0.3557 0.2495 0.033 Uiso 1 1 calc R
H12B H 1.4759 -0.2983 0.1388 0.033 Uiso 1 1 calc R
H12C H 1.6002 -0.4938 0.1555 0.033 Uiso 1 1 calc R
C13 C 1.21523(18) -0.23355(17) 0.30319(11) 0.0166(3) Uani 1 1 d .
H13 H 1.2847 -0.1719 0.3273 0.020 Uiso 1 1 calc R
C14 C 1.08958(18) -0.11916(17) 0.22825(11) 0.0165(3) Uani 1 1 d .
C15 C 0.93230(19) -0.13341(17) 0.20732(11) 0.0173(3) Uani 1 1 d .
C16 C 0.84328(19) 0.13086(17) 0.10325(11) 0.0164(3) Uani 1 1 d .
C17 C 1.13065(18) 0.01397(17) 0.18505(11) 0.0162(3) Uani 1 1 d .
C18 C 0.6502(2) -0.0143(2) 0.11654(13) 0.0243(3) Uani 1 1 d .
H18A H 0.5523 0.0601 0.1685 0.036 Uiso 1 1 calc R
H18B H 0.6625 -0.1309 0.1234 0.036 Uiso 1 1 calc R
H18C H 0.6253 0.0223 0.0407 0.036 Uiso 1 1 calc R
C19 C 1.0284(2) 0.28417(18) 0.08458(12) 0.0214(3) Uani 1 1 d .
H19A H 1.0138 0.2959 0.0051 0.032 Uiso 1 1 calc R
H19B H 1.1483 0.2693 0.0978 0.032 Uiso 1 1 calc R
H19C H 0.9413 0.3861 0.1247 0.032 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'
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
C1 N1 C12 114.71(11)
C1 N1 C11 108.01(11)
C12 N1 C11 108.86(11)
C1 N1 C13 103.96(10)
C12 N1 C13 109.86(10)
C11 N1 C13 111.39(10)
C16 N2 C17 124.23(11)
C16 N2 C19 116.72(11)
C17 N2 C19 118.94(11)
C16 N3 C15 124.03(12)
C16 N3 C18 116.88(12)
C15 N3 C18 119.05(11)
C2 C1 C9 121.77(13)
C2 C1 N1 129.18(13)
C9 C1 N1 108.74(12)
C1 C2 C3 116.59(14)
C4 C3 C2 122.73(14)
C3 C4 C10 120.46(13)
C6 C5 C10 119.97(13)
C5 C6 C7 122.55(14)
C8 C7 C6 118.56(13)
C7 C8 C9 118.63(13)
C7 C8 C13 131.91(13)
C9 C8 C13 109.10(12)
C1 C9 C8 113.07(13)
C1 C9 C10 122.49(13)
C8 C9 C10 124.43(14)
C9 C10 C5 115.85(13)
C9 C10 C4 115.93(14)
C5 C10 C4 128.20(13)
C14 C13 C8 121.21(12)
C14 C13 N1 115.54(11)
C8 C13 N1 101.36(10)
C15 C14 C17 122.05(12)
C15 C14 C13 122.14(12)
C17 C14 C13 115.66(12)
O3 C15 C14 126.33(13)
O3 C15 N3 117.27(12)
C14 C15 N3 116.40(12)
O2 C16 N2 121.52(12)
O2 C16 N3 121.52(13)
N2 C16 N3 116.96(12)
O1 C17 N2 118.38(12)
O1 C17 C14 125.42(13)
N2 C17 C14 116.17(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C17 1.2394(17)
O2 C16 1.2323(17)
O3 C15 1.2452(17)
N1 C1 1.4856(18)
N1 C12 1.4963(18)
N1 C11 1.5039(17)
N1 C13 1.6267(18)
N2 C16 1.3762(18)
N2 C17 1.4168(18)
N2 C19 1.4695(17)
N3 C16 1.3773(18)
N3 C15 1.4207(18)
N3 C18 1.4654(18)
C1 C2 1.364(2)
C1 C9 1.396(2)
C2 C3 1.426(2)
C3 C4 1.375(2)
C4 C10 1.425(2)
C5 C6 1.377(2)
C5 C10 1.418(2)
C6 C7 1.425(2)
C7 C8 1.367(2)
C8 C9 1.401(2)
C8 C13 1.5116(19)
C9 C10 1.406(2)
C13 C14 1.4774(19)
C14 C15 1.4111(19)
C14 C17 1.4229(19)
