#------------------------------------------------------------------------------
#$Date: 2022-06-21 12:13:29 +0300 (Tue, 21 Jun 2022) $
#$Revision: 276128 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105441.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_8105441
loop_
_publ_author_name
'Li-Hua, Wang'
'Xi-Shi, Tai'
_publ_section_title
;
 The crystal structure of
 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy)acetate,
 C19H18N2O3
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1275
_journal_page_last               1276
_journal_paper_doi               10.1515/ncrs-2020-0238
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 99.248(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6187(7)
_cell_length_b                   9.4445(5)
_cell_length_c                   13.7424(8)
_cell_measurement_reflns_used    3416
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4110
_cell_measurement_theta_min      3.5490
_cell_volume                     1616.49(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω      1.00  28.00   1.00    1.00    --   40.98 -99.00  60.00   27
  2  ω     54.00 100.00   1.00    1.00    --  106.95 -94.00 -30.00   46
  3  ω     34.00 128.00   1.00    1.00    --  106.95 -77.00-180.00   94
  4  ω     81.00 133.00   1.00    1.00    --  106.95  45.00-120.00   52
  5  ω    128.00 163.00   1.00    1.00    --  106.95 125.00-120.00   35
  6  ω    106.00 133.00   1.00    1.00    --  106.95 125.00-180.00   27
  7  ω     79.00 145.00   1.00    1.00    --  106.95  30.00  30.00   66
  8  ω     80.00 178.00   1.00    1.00    --  106.95  30.00 120.00   98
  9  ω    -36.00  -6.00   1.00    1.00    --  -40.98 125.00 -60.00   30
 10  ω   -114.00 -29.00   1.00    1.00    --  -40.98 -37.00 150.00   85
 11  ω   -102.00 -26.00   1.00    1.00    --  -40.98 -57.00-120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0302131000
_diffrn_orient_matrix_UB_12      -0.0690384000
_diffrn_orient_matrix_UB_13      0.1022274000
_diffrn_orient_matrix_UB_21      0.1173742000
_diffrn_orient_matrix_UB_22      -0.0134214000
_diffrn_orient_matrix_UB_23      -0.0169750000
_diffrn_orient_matrix_UB_31      0.0249360000
_diffrn_orient_matrix_UB_32      0.1471585000
_diffrn_orient_matrix_UB_33      0.0464145000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3187
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.546
_diffrn_reflns_theta_min         3.549
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.233
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.233
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0793
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0224P)²+5.6331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2193
_refine_ls_wR_factor_ref         0.2220
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2800
_reflns_number_total             3187
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0238_suppl.cif
_cod_data_source_block           wf_05_2
_cod_database_code               8105441
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.580(6)
 0.420(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C10(H10A,H10B), C11(H11A,H11B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16)
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5085(2) 0.1878(3) 0.3942(2) 0.0192(7) Uani 1 1 d . . . . .
O2 O 0.5907(2) 0.2430(3) 0.2318(2) 0.0189(6) Uani 1 1 d . . . . .
O3 O 0.4614(2) 0.1269(3) 0.1337(2) 0.0204(7) Uani 1 1 d . . . . .
N1 N 0.7459(3) 0.4256(4) 0.6624(3) 0.0179(8) Uani 1 1 d . . . . .
H1 H 0.705240 0.374543 0.692848 0.021 Uiso 1 1 calc R U . . .
N2 N 0.6697(3) 0.4037(4) 0.3903(3) 0.0156(7) Uani 1 1 d . . . . .
H2A H 0.636055 0.342872 0.346439 0.019 Uiso 1 1 calc R U . . .
H2B H 0.634804 0.485823 0.381910 0.019 Uiso 1 1 calc R U . . .
C1 C 0.9546(3) 0.6802(5) 0.6557(4) 0.0217(9) Uani 1 1 d . . . . .
H1A H 0.986453 0.724683 0.607410 0.026 Uiso 1 1 calc R U . . .
C2 C 0.9873(4) 0.7112(5) 0.7543(4) 0.0269(11) Uani 1 1 d . . . . .
H2 H 1.041296 0.777640 0.772051 0.032 Uiso 1 1 calc R U . . .
C3 C 0.9406(4) 0.6444(5) 0.8277(3) 0.0246(10) Uani 1 1 d . . . . .
H3 H 0.965523 0.665776 0.893496 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8582(4) 0.5471(5) 0.8049(3) 0.0226(10) Uani 1 1 d . . . . .
H4 H 0.826641 0.503344 0.853666 0.027 Uiso 1 1 calc R U . . .
C5 C 0.8249(3) 0.5180(5) 0.7055(3) 0.0172(9) Uani 1 1 d . . . . .
C6 C 0.8723(3) 0.5801(5) 0.6298(3) 0.0175(9) Uani 1 1 d . . . . .
C7 C 0.8202(3) 0.5205(4) 0.5382(3) 0.0165(9) Uani 1 1 d . . . . .
C8 C 0.7441(3) 0.4299(4) 0.5619(3) 0.0159(8) Uani 1 1 d . . . . .
C9 C 0.6636(3) 0.3492(4) 0.4924(3) 0.0156(8) Uani 1 1 d . . . . .
H9 H 0.592164 0.371503 0.507574 0.019 Uiso 1 1 calc R U . . .
C10 C 0.8363(3) 0.5439(5) 0.4334(3) 0.0188(9) Uani 1 1 d . . . . .
H10A H 0.912343 0.544360 0.429440 0.023 Uiso 1 1 calc R U . . .
H10B H 0.806251 0.634536 0.409979 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7805(3) 0.4249(5) 0.3698(3) 0.0197(9) Uani 1 1 d . . . . .
H11A H 0.778131 0.447998 0.300706 0.024 Uiso 1 1 calc R U . . .
H11B H 0.821106 0.337903 0.383305 0.024 Uiso 1 1 calc R U . . .
C12 C 0.6766(3) 0.1898(4) 0.4944(3) 0.0166(9) Uani 1 1 d . . . . .
C13 C 0.7628(4) 0.1195(5) 0.5491(3) 0.0209(9) Uani 1 1 d . . . . .
H13 H 0.817328 0.171751 0.586250 0.025 Uiso 1 1 calc R U . . .
C14 C 0.7691(4) -0.0271(5) 0.5496(3) 0.0231(10) Uani 1 1 d . . . . .
H14 H 0.827093 -0.072882 0.586909 0.028 Uiso 1 1 calc R U . . .
C15 C 0.6877(4) -0.1045(5) 0.4938(3) 0.0245(10) Uani 1 1 d . . . . .
H15 H 0.691570 -0.202852 0.493881 0.029 Uiso 1 1 calc R U . . .
C16 C 0.6005(4) -0.0379(5) 0.4378(3) 0.0214(9) Uani 1 1 d . . . . .
H16 H 0.546887 -0.090809 0.400016 0.026 Uiso 1 1 calc R U . . .
C17 C 0.5946(3) 0.1094(5) 0.4391(3) 0.0165(8) Uani 1 1 d . . . . .
C18 C 0.4487(3) 0.1378(5) 0.3038(3) 0.0220(10) Uani 1 1 d . . . . .
H18A H 0.378025 0.181005 0.293769 0.026 Uiso 1 1 calc R U . . .
H18B H 0.439335 0.036097 0.307890 0.026 Uiso 1 1 calc R U . . .
C19 C 0.5042(3) 0.1715(4) 0.2164(3) 0.0176(9) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C17 O1 C18 118.7(3) . .
C5 N1 H1 126.1 . .
C8 N1 H1 126.1 . .
C8 N1 C5 107.7(4) . .
H2A N2 H2B 107.6 . .
C9 N2 H2A 108.7 . .
C9 N2 H2B 108.7 . .
C11 N2 H2A 108.7 . .
C11 N2 H2B 108.7 . .
C11 N2 C9 114.4(3) . .
C2 C1 H1A 120.6 . .
C2 C1 C6 118.8(4) . .
C6 C1 H1A 120.6 . .
C1 C2 H2 119.4 . .
C1 C2 C3 121.2(4) . .
C3 C2 H2 119.4 . .
C2 C3 H3 119.2 . .
C4 C3 C2 121.5(4) . .
C4 C3 H3 119.2 . .
C3 C4 H4 121.6 . .
C3 C4 C5 116.8(4) . .
C5 C4 H4 121.6 . .
N1 C5 C4 128.9(4) . .
N1 C5 C6 108.0(4) . .
C4 C5 C6 123.1(4) . .
C1 C6 C5 118.5(4) . .
C1 C6 C7 134.4(4) . .
C5 C6 C7 107.1(4) . .
C6 C7 C10 131.9(4) . .
C8 C7 C6 106.1(4) . .
C8 C7 C10 122.0(4) . .
N1 C8 C9 121.8(4) . .
C7 C8 N1 111.1(4) . .
C7 C8 C9 127.0(4) . .
N2 C9 H9 108.1 . .
N2 C9 C12 109.5(3) . .
C8 C9 N2 106.9(3) . .
C8 C9 H9 108.1 . .
C8 C9 C12 115.9(4) . .
C12 C9 H9 108.1 . .
C7 C10 H10A 110.0 . .
C7 C10 H10B 110.0 . .
C7 C10 C11 108.7(4) . .
H10A C10 H10B 108.3 . .
C11 C10 H10A 110.0 . .
C11 C10 H10B 110.0 . .
N2 C11 C10 110.6(3) . .
N2 C11 H11A 109.5 . .
N2 C11 H11B 109.5 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 108.1 . .
C13 C12 C9 123.9(4) . .
C13 C12 C17 118.7(4) . .
C17 C12 C9 117.4(4) . .
C12 C13 H13 119.3 . .
C14 C13 C12 121.3(4) . .
C14 C13 H13 119.3 . .
C13 C14 H14 120.4 . .
C13 C14 C15 119.1(4) . .
C15 C14 H14 120.4 . .
C14 C15 H15 119.4 . .
C16 C15 C14 121.2(4) . .
C16 C15 H15 119.4 . .
C15 C16 H16 120.5 . .
C15 C16 C17 119.0(4) . .
C17 C16 H16 120.5 . .
O1 C17 C12 114.3(4) . .
O1 C17 C16 124.9(4) . .
C16 C17 C12 120.6(4) . .
O1 C18 H18A 109.2 . .
O1 C18 H18B 109.2 . .
O1 C18 C19 111.9(3) . .
H18A C18 H18B 107.9 . .
C19 C18 H18A 109.2 . .
C19 C18 H18B 109.2 . .
O2 C19 C18 118.2(4) . .
O3 C19 O2 124.4(4) . .
O3 C19 C18 117.4(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C17 1.376(5) .
O1 C18 1.427(5) .
O2 C19 1.272(5) .
O3 C19 1.250(5) .
N1 H1 0.8600 .
N1 C5 1.384(5) .
N1 C8 1.378(5) .
N2 H2A 0.8900 .
N2 H2B 0.8900 .
N2 C9 1.508(5) .
N2 C11 1.484(5) .
C1 H1A 0.9300 .
C1 C2 1.382(7) .
C1 C6 1.407(6) .
C2 H2 0.9300 .
C2 C3 1.398(7) .
C3 H3 0.9300 .
C3 C4 1.386(7) .
C4 H4 0.9300 .
C4 C5 1.390(6) .
C5 C6 1.409(6) .
C6 C7 1.438(6) .
C7 C8 1.364(6) .
C7 C10 1.504(6) .
C8 C9 1.487(6) .
C9 H9 0.9800 .
C9 C12 1.515(6) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 C11 1.524(6) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.388(6) .
C12 C17 1.404(6) .
C13 H13 0.9300 .
C13 C14 1.387(6) .
C14 H14 0.9300 .
C14 C15 1.388(7) .
C15 H15 0.9300 .
C15 C16 1.387(7) .
C16 H16 0.9300 .
C16 C17 1.394(6) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 C19 1.519(6) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C18 C19 O2 -3.2(6) . . . .
O1 C18 C19 O3 176.8(4) . . . .
N1 C5 C6 C1 179.2(4) . . . .
N1 C5 C6 C7 -0.8(5) . . . .
N1 C8 C9 N2 167.7(4) . . . .
N1 C8 C9 C12 -69.9(5) . . . .
N2 C9 C12 C13 114.9(4) . . . .
N2 C9 C12 C17 -66.8(5) . . . .
C1 C2 C3 C4 -1.5(7) . . . .
C1 C6 C7 C8 -178.7(5) . . . .
C1 C6 C7 C10 0.6(8) . . . .
C2 C1 C6 C5 1.5(6) . . . .
C2 C1 C6 C7 -178.6(5) . . . .
C2 C3 C4 C5 0.6(7) . . . .
C3 C4 C5 N1 179.4(4) . . . .
C3 C4 C5 C6 1.4(6) . . . .
C4 C5 C6 C1 -2.4(6) . . . .
C4 C5 C6 C7 177.6(4) . . . .
C5 N1 C8 C7 0.9(5) . . . .
C5 N1 C8 C9 -176.2(4) . . . .
C5 C6 C7 C8 1.3(5) . . . .
C5 C6 C7 C10 -179.4(4) . . . .
C6 C1 C2 C3 0.4(7) . . . .
C6 C7 C8 N1 -1.3(5) . . . .
C6 C7 C8 C9 175.6(4) . . . .
C6 C7 C10 C11 164.9(4) . . . .
C7 C8 C9 N2 -8.9(6) . . . .
C7 C8 C9 C12 113.5(5) . . . .
C7 C10 C11 N2 48.2(5) . . . .
C8 N1 C5 C4 -178.3(4) . . . .
C8 N1 C5 C6 0.0(5) . . . .
C8 C7 C10 C11 -15.9(6) . . . .
C8 C9 C12 C13 -6.1(6) . . . .
C8 C9 C12 C17 172.2(4) . . . .
C9 N2 C11 C10 -66.5(4) . . . .
C9 C12 C13 C14 178.6(4) . . . .
C9 C12 C17 O1 -3.7(5) . . . .
C9 C12 C17 C16 -179.5(4) . . . .
C10 C7 C8 N1 179.3(4) . . . .
C10 C7 C8 C9 -3.8(7) . . . .
C11 N2 C9 C8 43.3(4) . . . .
C11 N2 C9 C12 -83.1(4) . . . .
C12 C13 C14 C15 0.3(7) . . . .
C13 C12 C17 O1 174.7(4) . . . .
C13 C12 C17 C16 -1.1(6) . . . .
C13 C14 C15 C16 0.0(7) . . . .
C14 C15 C16 C17 -0.8(7) . . . .
C15 C16 C17 O1 -173.9(4) . . . .
C15 C16 C17 C12 1.4(6) . . . .
C17 O1 C18 C19 -79.9(5) . . . .
C17 C12 C13 C14 0.3(7) . . . .
C18 O1 C17 C12 150.2(4) . . . .
C18 O1 C17 C16 -34.2(6) . . . .
