#------------------------------------------------------------------------------
#$Date: 2022-03-29 10:52:40 +0300 (Tue, 29 Mar 2022) $
#$Revision: 274069 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104915.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_8104915
loop_
_publ_author_name
'Kailani, Mohammed H.'
'Awwadi, Firas F.'
_publ_section_title
;
 4-(9H-Fluoren-9-yl)-4-methylmorpholin-4-ium bromide, C18H20BrNO
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              179
_journal_page_last               180
_journal_paper_doi               10.1515/ncrs-2020-0436
_journal_volume                  236
_journal_year                    2021
_chemical_formula_sum            'C18 H20 Br N O'
_chemical_formula_weight         346.26
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.4285(4)
_cell_length_b                   19.2055(9)
_cell_length_c                   19.7809(12)
_cell_measurement_reflns_used    1514
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1594
_cell_measurement_theta_min      2.9507
_cell_volume                     3202.0(3)
_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_molecular_graphics    'shelxtl, Bruker,2002'
_computing_publication_material  'shelxtl, Bruker,2002'
_computing_structure_refinement  'shelxtl, Bruker,2002'
_computing_structure_solution    'shelxtl, Bruker,2002'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0534
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos'
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9934
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.30
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    2.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66128
_exptl_absorpt_correction_type   multi-scan
_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            white
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0427
_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)+(0.0418P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                2038
_reflns_number_total             3252
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_j_ncrs-2020-0436_suppl.cif
_cod_data_source_block           exp797
_cod_database_code               8104915
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.27202(4) 0.124219(18) 0.496124(15) 0.04542(14) Uani 1 1 d . . .
C1 C 0.7239(4) 0.18858(17) 0.47311(14) 0.0396(8) Uani 1 1 d . . .
H1A H 0.6141 0.1940 0.4868 0.048 Uiso 1 1 calc R . .
H1B H 0.7532 0.2292 0.4468 0.048 Uiso 1 1 calc R . .
C2 C 0.8267(4) 0.18496(17) 0.53505(13) 0.0478(8) Uani 1 1 d . . .
H2A H 0.9371 0.1821 0.5215 0.057 Uiso 1 1 calc R . .
H2B H 0.8131 0.2272 0.5614 0.057 Uiso 1 1 calc R . .
C3 C 0.8175(4) 0.06494(16) 0.53716(14) 0.0465(8) Uani 1 1 d . . .
H3A H 0.7970 0.0242 0.5648 0.056 Uiso 1 1 calc R . .
H3B H 0.9282 0.0639 0.5237 0.056 Uiso 1 1 calc R . .
C4 C 0.7136(4) 0.06277(17) 0.47508(14) 0.0400(8) Uani 1 1 d . . .
H4A H 0.7360 0.0205 0.4499 0.048 Uiso 1 1 calc R . .
H4B H 0.6033 0.0612 0.4889 0.048 Uiso 1 1 calc R . .
C5 C 0.8970(3) 0.12153(18) 0.39548(13) 0.0481(9) Uani 1 1 d . . .
H5A H 0.9115 0.1622 0.3680 0.072 Uiso 1 1 calc R . .
H5B H 0.9020 0.0807 0.3675 0.072 Uiso 1 1 calc R . .
H5C H 0.9792 0.1195 0.4290 0.072 Uiso 1 1 calc R . .
C6 C 0.6053(3) 0.12686(15) 0.37476(11) 0.0296(6) Uani 1 1 d . . .
H6 H 0.5011 0.1311 0.3963 0.036 Uiso 1 1 calc R . .
C7 C 0.6303(3) 0.18594(15) 0.32504(12) 0.0308(7) Uani 1 1 d . . .
C8 C 0.6650(3) 0.15827(16) 0.26120(13) 0.0327(7) Uani 1 1 d . . .
C9 C 0.6511(3) 0.08278(17) 0.26382(13) 0.0347(7) Uani 1 1 d . . .
C10 C 0.6096(3) 0.06295(15) 0.32976(12) 0.0318(7) Uani 1 1 d . . .
C11 C 0.5731(3) -0.00549(17) 0.34339(15) 0.0455(8) Uani 1 1 d . . .
H11 H 0.5410 -0.0186 0.3865 0.055 Uiso 1 1 calc R . .
C12 C 0.5846(4) -0.05482(19) 0.29233(16) 0.0587(10) Uani 1 1 d . . .
H12 H 0.5605 -0.1012 0.3012 0.070 Uiso 1 1 calc R . .
C13 C 0.6321(4) -0.03478(19) 0.22790(16) 0.0593(10) Uani 1 1 d . . .
H13 H 0.6412 -0.0682 0.1941 0.071 Uiso 1 1 calc R . .
C14 C 0.6654(4) 0.03280(19) 0.21334(14) 0.0492(9) Uani 1 1 d . . .
H14 H 0.6974 0.0455 0.1701 0.059 Uiso 1 1 calc R . .
C15 C 0.6950(4) 0.20249(18) 0.20700(13) 0.0459(8) Uani 1 1 d . . .
H15 H 0.7207 0.1845 0.1648 0.055 Uiso 1 1 calc R . .
C16 C 0.6861(4) 0.27306(18) 0.21682(15) 0.0545(9) Uani 1 1 d . . .
H16 H 0.7062 0.3030 0.1808 0.065 Uiso 1 1 calc R . .
C17 C 0.6479(4) 0.30040(18) 0.27922(14) 0.0505(9) Uani 1 1 d . . .
H17 H 0.6409 0.3484 0.2847 0.061 Uiso 1 1 calc R . .
C18 C 0.6198(3) 0.25672(16) 0.33375(13) 0.0396(7) Uani 1 1 d . . .
H18 H 0.5941 0.2752 0.3758 0.048 Uiso 1 1 calc R . .
N1 N 0.7387(2) 0.12486(13) 0.42956(11) 0.0288(5) Uani 1 1 d . . .
O1 O 0.7878(3) 0.12632(12) 0.57565(10) 0.0504(6) 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'
Br Br -0.2901 2.4595 '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
C2 O1 C3 108.2(2) . .
O1 C2 C1 111.4(3) . .
O1 C2 H2A 109.4 . .
C1 C2 H2A 109.4 . .
O1 C2 H2B 109.4 . .
C1 C2 H2B 109.4 . .
H2A C2 H2B 108.0 . .
N1 C1 C2 112.5(2) . .
N1 C1 H1A 109.1 . .
C2 C1 H1A 109.1 . .
N1 C1 H1B 109.1 . .
C2 C1 H1B 109.1 . .
H1A C1 H1B 107.8 . .
C5 N1 C1 111.6(2) . .
C5 N1 C4 111.1(2) . .
C1 N1 C4 106.9(2) . .
C5 N1 C6 109.28(19) . .
C1 N1 C6 108.5(2) . .
C4 N1 C6 109.4(2) . .
N1 C4 C3 112.5(2) . .
N1 C4 H4A 109.1 . .
C3 C4 H4A 109.1 . .
N1 C4 H4B 109.1 . .
C3 C4 H4B 109.1 . .
H4A C4 H4B 107.8 . .
O1 C3 C4 110.8(2) . .
O1 C3 H3A 109.5 . .
C4 C3 H3A 109.5 . .
O1 C3 H3B 109.5 . .
C4 C3 H3B 109.5 . .
H3A C3 H3B 108.1 . .
C7 C6 C10 102.8(2) . .
C7 C6 N1 111.6(2) . .
C10 C6 N1 111.7(2) . .
C7 C6 H6 110.2 . .
C10 C6 H6 110.2 . .
N1 C6 H6 110.2 . .
C11 C10 C9 119.8(3) . .
C11 C10 C6 130.7(3) . .
C9 C10 C6 109.4(3) . .
C10 C11 C12 119.6(3) . .
C10 C11 H11 120.2 . .
C12 C11 H11 120.2 . .
C11 C12 C13 119.9(3) . .
C11 C12 H12 120.1 . .
C13 C12 H12 120.1 . .
C14 C13 C12 121.2(3) . .
C14 C13 H13 119.4 . .
C12 C13 H13 119.4 . .
C13 C14 C9 119.3(3) . .
C13 C14 H14 120.4 . .
C9 C14 H14 120.4 . .
C14 C9 C10 120.1(3) . .
C14 C9 C8 130.9(3) . .
C10 C9 C8 108.9(2) . .
C15 C8 C7 120.1(3) . .
C15 C8 C9 130.6(3) . .
C7 C8 C9 109.2(2) . .
C16 C15 C8 119.0(3) . .
C16 C15 H15 120.5 . .
C8 C15 H15 120.5 . .
C15 C16 C17 121.0(3) . .
C15 C16 H16 119.5 . .
C17 C16 H16 119.5 . .
C16 C17 C18 120.4(3) . .
C16 C17 H17 119.8 . .
C18 C17 H17 119.8 . .
C7 C18 C17 119.3(3) . .
C7 C18 H18 120.3 . .
C17 C18 H18 120.3 . .
C18 C7 C8 120.1(3) . .
C18 C7 C6 130.6(2) . .
C8 C7 C6 109.3(3) . .
N1 C5 H5A 109.5 . .
N1 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
N1 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.421(3) .
O1 C3 1.426(3) .
C2 C1 1.502(4) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C1 N1 1.502(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
N1 C5 1.496(3) .
N1 C4 1.509(3) .
N1 C6 1.562(3) .
C4 C3 1.509(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C6 C7 1.516(3) .
C6 C10 1.517(3) .
C6 H6 0.9800 .
C10 C11 1.377(4) .
C10 C9 1.403(3) .
C11 C12 1.388(4) .
C11 H11 0.9300 .
C12 C13 1.390(4) .
C12 H12 0.9300 .
C13 C14 1.359(5) .
C13 H13 0.9300 .
C14 C9 1.390(4) .
C14 H14 0.9300 .
C9 C8 1.455(4) .
C8 C15 1.391(4) .
C8 C7 1.401(3) .
C15 C16 1.371(4) .
C15 H15 0.9300 .
C16 C17 1.380(4) .
C16 H16 0.9300 .
C17 C18 1.387(4) .
C17 H17 0.9300 .
C18 C7 1.373(4) .
C18 H18 0.9300 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
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
C3 O1 C2 C1 62.4(3) . . . .
O1 C2 C1 N1 -59.1(4) . . . .
C2 C1 N1 C5 -70.3(3) . . . .
C2 C1 N1 C4 51.3(3) . . . .
C2 C1 N1 C6 169.2(2) . . . .
C5 N1 C4 C3 70.5(3) . . . .
C1 N1 C4 C3 -51.4(3) . . . .
C6 N1 C4 C3 -168.7(2) . . . .
C2 O1 C3 C4 -62.1(3) . . . .
N1 C4 C3 O1 58.9(4) . . . .
C5 N1 C6 C7 -54.8(3) . . . .
C1 N1 C6 C7 67.1(3) . . . .
C4 N1 C6 C7 -176.7(2) . . . .
C5 N1 C6 C10 59.7(3) . . . .
C1 N1 C6 C10 -178.4(2) . . . .
C4 N1 C6 C10 -62.2(3) . . . .
C7 C6 C10 C11 -170.1(3) . . . .
N1 C6 C10 C11 70.0(4) . . . .
C7 C6 C10 C9 6.3(3) . . . .
N1 C6 C10 C9 -113.5(2) . . . .
C9 C10 C11 C12 2.8(4) . . . .
C6 C10 C11 C12 179.0(3) . . . .
C10 C11 C12 C13 -0.2(5) . . . .
C11 C12 C13 C14 -1.1(5) . . . .
C12 C13 C14 C9 -0.2(5) . . . .
C13 C14 C9 C10 2.9(4) . . . .
C13 C14 C9 C8 -173.8(3) . . . .
C11 C10 C9 C14 -4.2(4) . . . .
C6 C10 C9 C14 178.9(2) . . . .
C11 C10 C9 C8 173.2(3) . . . .
C6 C10 C9 C8 -3.7(3) . . . .
C14 C9 C8 C15 0.8(5) . . . .
C10 C9 C8 C15 -176.2(3) . . . .
C14 C9 C8 C7 176.2(3) . . . .
C10 C9 C8 C7 -0.8(3) . . . .
C7 C8 C15 C16 -1.6(5) . . . .
C9 C8 C15 C16 173.3(3) . . . .
C8 C15 C16 C17 -0.1(5) . . . .
C15 C16 C17 C18 0.9(5) . . . .
C16 C17 C18 C7 0.0(5) . . . .
C17 C18 C7 C8 -1.7(4) . . . .
C17 C18 C7 C6 -179.6(3) . . . .
C15 C8 C7 C18 2.5(4) . . . .
C9 C8 C7 C18 -173.4(3) . . . .
C15 C8 C7 C6 -179.1(2) . . . .
C9 C8 C7 C6 4.9(3) . . . .
C10 C6 C7 C18 171.3(3) . . . .
N1 C6 C7 C18 -68.8(4) . . . .
C10 C6 C7 C8 -6.8(3) . . . .
N1 C6 C7 C8 113.1(2) . . . .
