#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/26/7152631.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_7152631
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         'C22 H17 N O2'
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.37
_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                 95.980(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8717(3)
_cell_length_b                   11.5384(3)
_cell_length_c                   15.6190(5)
_cell_measurement_reflns_used    4313
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.04
_cell_measurement_theta_min      3.15
_cell_volume                     1590.14(9)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7969
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-89
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0387
_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)+(0.0482P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                2836
_reflns_number_total             3648
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25929j.txt
_cod_data_source_block           compound_13
_cod_original_cell_volume        1590.14(8)
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7152631
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
O1 O 0.39284(10) 0.84108(7) 0.06104(5) 0.0255(2) Uani 1 1 d .
O2 O 0.52011(10) 0.59832(7) -0.16487(6) 0.0285(2) Uani 1 1 d .
N1 N 0.32162(11) 0.88040(8) -0.19149(6) 0.0178(2) Uani 1 1 d .
C1 C 0.18681(14) 0.95584(9) -0.19523(7) 0.0174(3) Uani 1 1 d .
C2 C 0.15700(15) 1.05357(10) -0.24278(8) 0.0227(3) Uani 1 1 d .
H2 H 0.2244 1.0813 -0.2816 0.027 Uiso 1 1 calc R
C3 C 0.01942(15) 1.11188(11) -0.23115(8) 0.0265(3) Uani 1 1 d .
H3 H -0.0052 1.1803 -0.2635 0.032 Uiso 1 1 calc R
C4 C -0.07933(15) 1.07368(11) -0.17521(8) 0.0253(3) Uani 1 1 d .
H4 H -0.1699 1.1157 -0.1696 0.030 Uiso 1 1 calc R
C5 C -0.13381(14) 0.92228(11) -0.06374(8) 0.0224(3) Uani 1 1 d .
H5 H -0.2272 0.9566 -0.0526 0.027 Uiso 1 1 calc R
C6 C -0.08227(14) 0.82460(11) -0.01994(8) 0.0231(3) Uani 1 1 d .
H6 H -0.1409 0.7933 0.0221 0.028 Uiso 1 1 calc R
C7 C 0.05476(14) 0.76842(10) -0.03470(8) 0.0207(3) Uani 1 1 d .
H7 H 0.0868 0.7005 -0.0035 0.025 Uiso 1 1 calc R
C8 C 0.13999(13) 0.81379(9) -0.09472(7) 0.0166(3) Uani 1 1 d .
C9 C 0.08835(13) 0.91468(9) -0.13842(7) 0.0167(3) Uani 1 1 d .
C10 C -0.04687(14) 0.97173(10) -0.12569(8) 0.0200(3) Uani 1 1 d .
C12 C 0.34606(17) 0.83527(11) -0.27892(8) 0.0287(3) Uani 1 1 d .
H12A H 0.2497 0.8070 -0.3078 0.043 Uiso 1 1 calc R
H12B H 0.4195 0.7716 -0.2731 0.043 Uiso 1 1 calc R
H12C H 0.3849 0.8977 -0.3131 0.043 Uiso 1 1 calc R
C11 C 0.45874(15) 0.94495(11) -0.15399(9) 0.0301(3) Uani 1 1 d .
H11A H 0.4770 1.0109 -0.1911 0.045 Uiso 1 1 calc R
H11B H 0.5468 0.8932 -0.1498 0.045 Uiso 1 1 calc R
H11C H 0.4425 0.9732 -0.0965 0.045 Uiso 1 1 calc R
C13 C 0.28282(13) 0.77073(9) -0.12925(7) 0.0162(3) Uani 1 1 d .
H13 H 0.2528 0.7040 -0.1682 0.019 Uiso 1 1 calc R
C14 C 0.41117(14) 0.73165(9) -0.06974(7) 0.0168(3) Uani 1 1 d .
C15 C 0.51376(14) 0.64493(10) -0.09352(8) 0.0191(3) Uani 1 1 d .
C16 C 0.62212(14) 0.62024(10) -0.01476(8) 0.0190(3) Uani 1 1 d .
C17 C 0.74217(14) 0.54413(10) -0.00278(8) 0.0247(3) Uani 1 1 d .
H17 H 0.7660 0.4940 -0.0477 0.030 Uiso 1 1 calc R
C18 C 0.82800(15) 0.54294(11) 0.07777(9) 0.0281(3) Uani 1 1 d .
H18 H 0.9105 0.4905 0.0880 0.034 Uiso 1 1 calc R
C19 C 0.79393(15) 0.61722(11) 0.14260(8) 0.0266(3) Uani 1 1 d .
H19 H 0.8540 0.6156 0.1966 0.032 Uiso 1 1 calc R
C20 C 0.67260(14) 0.69439(11) 0.12980(8) 0.0226(3) Uani 1 1 d .
H20 H 0.6499 0.7459 0.1741 0.027 Uiso 1 1 calc R
C21 C 0.58632(14) 0.69382(10) 0.05080(8) 0.0182(3) Uani 1 1 d .
C22 C 0.45070(14) 0.76674(10) 0.01746(8) 0.0181(3) 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
C1 N1 C11 110.19(9)
C1 N1 C12 111.26(9)
C11 N1 C12 109.97(10)
C1 N1 C13 104.91(8)
C11 N1 C13 111.23(8)
C12 N1 C13 109.19(8)
C2 C1 C9 122.10(12)
C2 C1 N1 128.40(11)
C9 C1 N1 109.47(9)
C1 C2 C3 116.30(12)
C4 C3 C2 122.86(12)
C3 C4 C10 120.38(12)
C6 C5 C10 119.60(12)
C5 C6 C7 122.79(12)
C8 C7 C6 118.74(11)
C7 C8 C9 118.38(11)
C7 C8 C13 131.46(10)
C9 C8 C13 110.04(10)
C1 C9 C10 122.26(11)
C1 C9 C8 113.50(11)
C10 C9 C8 124.23(11)
C9 C10 C5 116.25(11)
C9 C10 C4 116.10(12)
C5 C10 C4 127.63(12)
C14 C13 C8 120.00(10)
C14 C13 N1 114.41(9)
C8 C13 N1 101.06(8)
C15 C14 C22 110.28(11)
C15 C14 C13 121.71(11)
C22 C14 C13 127.96(11)
O2 C15 C14 128.73(11)
O2 C15 C16 124.39(11)
C14 C15 C16 106.85(10)
C17 C16 C21 121.41(11)
C17 C16 C15 130.50(11)
C21 C16 C15 108.06(10)
C16 C17 C18 117.91(12)
C19 C18 C17 120.75(12)
C18 C19 C20 120.96(12)
C21 C20 C19 118.16(12)
C20 C21 C16 120.78(11)
C20 C21 C22 130.54(11)
C16 C21 C22 108.64(10)
O1 C22 C14 130.17(11)
O1 C22 C21 123.72(11)
C14 C22 C21 106.11(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C22 1.2391(14)
O2 C15 1.2441(14)
N1 C1 1.4754(15)
N1 C11 1.4930(15)
N1 C12 1.4983(15)
N1 C13 1.6536(14)
C1 C2 1.3609(16)
C1 C9 1.3920(16)
C2 C3 1.4218(18)
C3 C4 1.3729(18)
C4 C10 1.4207(17)
C5 C6 1.3719(17)
C5 C10 1.4186(17)
C6 C7 1.4176(17)
C7 C8 1.3684(16)
C8 C9 1.4020(16)
C8 C13 1.5119(16)
C9 C10 1.4006(16)
C13 C14 1.4640(16)
C14 C15 1.4275(16)
C14 C22 1.4292(17)
C15 C16 1.5073(16)
C16 C17 1.3781(17)
C16 C21 1.3921(17)
C17 C18 1.4012(18)
C18 C19 1.3837(19)
C19 C20 1.3953(18)
C20 C21 1.3826(16)
C21 C22 1.5153(17)
