#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:43:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180312 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/26/7152626.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_7152626
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         'C13 H14 N O, Cl'
_chemical_formula_sum            'C13 H14 Cl N O'
_chemical_formula_weight         235.70
_chemical_name_systematic
;
2-Hydroxy-1,1-dimethyl-1,2-dihydrobenzo[cd]indol-1-ium chloride
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.9646(4)
_cell_length_b                   11.9986(5)
_cell_length_c                   19.3145(7)
_cell_measurement_reflns_used    2868
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.09
_cell_measurement_theta_min      2.85
_cell_volume                     2309.27(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.98
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.871
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7569
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98426
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0447
_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)+(0.0358P)²+0.7501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                2301
_reflns_number_total             2708
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25929j.txt
_cod_data_source_block           compound_7Cl
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7152626
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
Cl1 Cl -0.17574(5) 0.96972(4) 0.22215(2) 0.02765(14) Uani 1 1 d .
O1 O 0.02398(13) 0.91445(10) 0.11623(6) 0.0272(3) Uani 1 1 d .
H1 H -0.0225 0.9374 0.1496 0.033 Uiso 1 1 calc R
N1 N 0.04645(13) 0.71213(11) 0.13969(7) 0.0177(3) Uani 1 1 d .
C1 C 0.09674(16) 0.63381(14) 0.08645(8) 0.0176(3) Uani 1 1 d .
C2 C 0.15422(17) 0.53254(14) 0.09548(9) 0.0225(4) Uani 1 1 d .
H2 H 0.1647 0.5001 0.1400 0.027 Uiso 1 1 calc R
C3 C 0.19787(18) 0.47776(15) 0.03419(9) 0.0243(4) Uani 1 1 d .
H3 H 0.2372 0.4059 0.0383 0.029 Uiso 1 1 calc R
C4 C 0.18606(17) 0.52336(14) -0.03047(9) 0.0233(4) Uani 1 1 d .
H4 H 0.2195 0.4841 -0.0696 0.028 Uiso 1 1 calc R
C5 C 0.10156(18) 0.68782(15) -0.10193(9) 0.0256(4) Uani 1 1 d .
H5 H 0.1287 0.6566 -0.1449 0.031 Uiso 1 1 calc R
C6 C 0.04003(19) 0.79047(16) -0.10014(9) 0.0288(4) Uani 1 1 d .
H6 H 0.0271 0.8294 -0.1425 0.035 Uiso 1 1 calc R
C7 C -0.00467(19) 0.84044(16) -0.03816(9) 0.0258(4) Uani 1 1 d .
H7 H -0.0479 0.9110 -0.0386 0.031 Uiso 1 1 calc R
C8 C 0.01602(17) 0.78430(14) 0.02242(9) 0.0201(4) Uani 1 1 d .
C9 C 0.07966(16) 0.68101(14) 0.02137(8) 0.0168(3) Uani 1 1 d .
C10 C 0.12428(17) 0.62883(14) -0.03950(8) 0.0203(4) Uani 1 1 d .
C13 C -0.02206(17) 0.81376(14) 0.09546(8) 0.0206(4) Uani 1 1 d .
H13 H -0.1219 0.8110 0.1006 0.025 Uiso 1 1 calc R
C12 C -0.05761(19) 0.66076(15) 0.18566(9) 0.0266(4) Uani 1 1 d .
H12A H -0.1313 0.6317 0.1573 0.040 Uiso 1 1 calc R
H12C H -0.0924 0.7173 0.2176 0.040 Uiso 1 1 calc R
H12B H -0.0173 0.5997 0.2122 0.040 Uiso 1 1 calc R
C11 C 0.15996(19) 0.75415(15) 0.18323(9) 0.0277(4) Uani 1 1 d .
H11B H 0.1983 0.6923 0.2098 0.042 Uiso 1 1 calc R
H11C H 0.1267 0.8113 0.2151 0.042 Uiso 1 1 calc R
H11A H 0.2292 0.7864 0.1533 0.042 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'
Cl Cl 0.1484 0.1585 '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
C13 O1 H1 109.5
C1 N1 C11 110.38(13)
C1 N1 C12 112.63(13)
C11 N1 C12 109.19(13)
C1 N1 C13 104.56(11)
C11 N1 C13 110.93(13)
C12 N1 C13 109.09(13)
C2 C1 C9 122.28(15)
C2 C1 N1 128.54(15)
C9 C1 N1 109.16(14)
C1 C2 C3 115.89(16)
C1 C2 H2 122.1
C3 C2 H2 122.1
C4 C3 C2 123.27(16)
C4 C3 H3 118.4
C2 C3 H3 118.4
C3 C4 C10 120.42(16)
C3 C4 H4 119.8
C10 C4 H4 119.8
C6 C5 C10 119.81(16)
C6 C5 H5 120.1
C10 C5 H5 120.1
C5 C6 C7 122.83(17)
C5 C6 H6 118.6
C7 C6 H6 118.6
C8 C7 C6 118.01(17)
C8 C7 H7 121.0
C6 C7 H7 121.0
C7 C8 C9 119.69(16)
C7 C8 C13 130.55(16)
C9 C8 C13 109.75(14)
C1 C9 C8 113.93(14)
C1 C9 C10 122.48(16)
C8 C9 C10 123.59(15)
C9 C10 C5 116.06(16)
C9 C10 C4 115.62(15)
C5 C10 C4 128.32(16)
O1 C13 C8 113.75(14)
O1 C13 N1 111.63(13)
C8 C13 N1 102.08(13)
O1 C13 H13 109.7
C8 C13 H13 109.7
N1 C13 H13 109.7
N1 C12 H12A 109.5
N1 C12 H12C 109.5
H12A C12 H12C 109.5
N1 C12 H12B 109.5
H12A C12 H12B 109.5
H12C C12 H12B 109.5
N1 C11 H11B 109.5
N1 C11 H11C 109.5
H11B C11 H11C 109.5
N1 C11 H11A 109.5
H11B C11 H11A 109.5
H11C C11 H11A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.353(2)
O1 H1 0.8400
N1 C1 1.480(2)
N1 C11 1.497(2)
N1 C12 1.498(2)
N1 C13 1.638(2)
C1 C2 1.355(2)
C1 C9 1.389(2)
C2 C3 1.422(2)
C2 H2 0.9500
C3 C4 1.368(2)
C3 H3 0.9500
C4 C10 1.418(2)
C4 H4 0.9500
C5 C6 1.376(3)
C5 C10 1.416(2)
C5 H5 0.9500
C6 C7 1.411(2)
C6 H6 0.9500
C7 C8 1.366(2)
C7 H7 0.9500
C8 C9 1.392(2)
C8 C13 1.503(2)
C9 C10 1.404(2)
C13 H13 1.0000
C12 H12A 0.9800
C12 H12C 0.9800
C12 H12B 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C11 H11A 0.9800
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
O1 H1 Cl1 0.84 2.11 2.9302(13) 165.8
