#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/85/2228578.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_2228578
loop_
_publ_author_name
'Lin, Songzhu'
'Jia, Ruokun'
'Gao, Xiaoli'
'Yu, Haihui'
'Yuan, Yanlin'
_publ_section_title
;
 4-[(9-Ethyl-9H-carbazol-3-yl)iminomethyl]phenol
;
_journal_coeditor_code           VM2053
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3194
_journal_paper_doi               10.1107/S1600536810046167
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H18 N2 O'
_chemical_formula_moiety         'C21 H18 N2 O'
_chemical_formula_sum            'C21 H18 N2 O'
_chemical_formula_weight         314.37
_chemical_name_systematic
;
4-[(9-Ethyl-9H-carbazol-3-yl)iminomethyl]phenol
;
_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                   13.386(6)
_cell_length_b                   9.247(4)
_cell_length_c                   26.443(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      4
_cell_volume                     3273(2)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al., 1989)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω
_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  0.0810
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21605
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.176
_refine_ls_extinction_coef       0.0037(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0497
_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)+(0.0568P)²+0.6129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                1615
_reflns_number_total             2878
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            vm2053.cif
_cod_data_source_block           I
_cod_database_code               2228578
_cod_database_fobs_code          2228578
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.61757(15) 0.7932(2) 0.83217(7) 0.0802(7) Uani d . 1 . .
H H1 0.5624 0.8316 0.8314 0.096 Uiso calc R 1 . .
N N1 0.64140(15) 0.0252(2) 0.47293(8) 0.0538(6) Uani d . 1 . .
N N2 0.58786(17) 0.3455(2) 0.64785(8) 0.0580(6) Uani d . 1 . .
C C1 0.7978(2) -0.0332(4) 0.42951(13) 0.0866(10) Uani d . 1 . .
H H1A 0.8397 -0.1123 0.4193 0.130 Uiso calc R 1 . .
H H1B 0.8343 0.0292 0.4519 0.130 Uiso calc R 1 . .
H H1C 0.7772 0.0202 0.4002 0.130 Uiso calc R 1 . .
C C2 0.7074(2) -0.0908(3) 0.45633(11) 0.0639(8) Uani d . 1 . .
H H2B 0.6711 -0.1547 0.4338 0.077 Uiso calc R 1 . .
H H2C 0.7285 -0.1468 0.4855 0.077 Uiso calc R 1 . .
C C3 0.57518(18) 0.0966(3) 0.44114(10) 0.0509(7) Uani d . 1 . .
C C4 0.5568(2) 0.0753(3) 0.39037(11) 0.0635(8) Uani d . 1 . .
H H4A 0.5892 0.0024 0.3725 0.076 Uiso calc R 1 . .
C C5 0.4897(2) 0.1644(3) 0.36707(12) 0.0710(9) Uani d . 1 . .
H H5A 0.4767 0.1523 0.3328 0.085 Uiso calc R 1 . .
C C6 0.4407(2) 0.2721(3) 0.39335(12) 0.0692(8) Uani d . 1 . .
H H6A 0.3953 0.3310 0.3765 0.083 Uiso calc R 1 . .
C C7 0.45795(19) 0.2937(3) 0.44390(11) 0.0605(7) Uani d . 1 . .
H H7A 0.4241 0.3658 0.4614 0.073 Uiso calc R 1 . .
C C8 0.52679(18) 0.2060(3) 0.46856(10) 0.0473(6) Uani d . 1 . .
C C9 0.56752(17) 0.2025(3) 0.51875(9) 0.0462(6) Uani d . 1 . .
C C10 0.55122(17) 0.2834(3) 0.56227(10) 0.0509(7) Uani d . 1 . .
H H10A 0.5030 0.3558 0.5624 0.061 Uiso calc R 1 . .
C C11 0.60673(19) 0.2563(3) 0.60528(10) 0.0518(7) Uani d . 1 . .
C C12 0.6761(2) 0.1429(3) 0.60559(10) 0.0576(7) Uani d . 1 . .
H H12A 0.7122 0.1242 0.6349 0.069 Uiso calc R 1 . .
C C13 0.69205(19) 0.0585(3) 0.56350(11) 0.0579(7) Uani d . 1 . .
H H13A 0.7376 -0.0174 0.5642 0.069 Uiso calc R 1 . .
C C14 0.63826(18) 0.0899(3) 0.51982(10) 0.0492(7) Uani d . 1 . .
C C15 0.6605(2) 0.3883(3) 0.67601(11) 0.0613(8) Uani d . 1 . .
H H15A 0.7244 0.3539 0.6692 0.074 Uiso calc R 1 . .
C C16 0.6471(2) 0.4883(3) 0.71814(10) 0.0593(7) Uani d . 1 . .
C C17 0.7279(2) 0.5339(3) 0.74665(11) 0.0716(9) Uani d . 1 . .
H H17A 0.7907 0.4947 0.7404 0.086 Uiso calc R 1 . .
C C18 0.7171(2) 0.6370(4) 0.78447(11) 0.0741(9) Uani d . 1 . .
H H18A 0.7724 0.6675 0.8029 0.089 Uiso calc R 1 . .
C C19 0.6242(2) 0.6938(3) 0.79452(10) 0.0624(8) Uani d . 1 . .
C C20 0.5425(2) 0.6490(3) 0.76697(11) 0.0685(8) Uani d . 1 . .
H H20A 0.4795 0.6866 0.7739 0.082 Uiso calc R 1 . .
C C21 0.5548(2) 0.5481(3) 0.72916(11) 0.0684(8) Uani d . 1 . .
H H21A 0.4994 0.5192 0.7105 0.082 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C19 O1 H1 . . 109.5 ?
C14 N1 C3 . . 108.6(2) ?
C14 N1 C2 . . 127.6(2) ?
C3 N1 C2 . . 123.7(2) ?
C15 N2 C11 . . 120.2(2) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 C1 . . 111.7(2) ?
N1 C2 H2B . . 109.3 ?
C1 C2 H2B . . 109.3 ?
N1 C2 H2C . . 109.3 ?
C1 C2 H2C . . 109.3 ?
H2B C2 H2C . . 107.9 ?
C4 C3 N1 . . 129.4(2) ?
C4 C3 C8 . . 121.6(3) ?
N1 C3 C8 . . 109.0(2) ?
C5 C4 C3 . . 118.0(3) ?
C5 C4 H4A . . 121.0 ?
C3 C4 H4A . . 121.0 ?
C4 C5 C6 . . 121.4(3) ?
C4 C5 H5A . . 119.3 ?
C6 C5 H5A . . 119.3 ?
C7 C6 C5 . . 121.1(3) ?
C7 C6 H6A . . 119.5 ?
C5 C6 H6A . . 119.5 ?
C6 C7 C8 . . 118.9(3) ?
C6 C7 H7A . . 120.5 ?
C8 C7 H7A . . 120.5 ?
C7 C8 C3 . . 119.0(3) ?
C7 C8 C9 . . 134.3(2) ?
C3 C8 C9 . . 106.6(2) ?
C10 C9 C14 . . 119.2(2) ?
C10 C9 C8 . . 133.9(2) ?
C14 C9 C8 . . 106.9(2) ?
C11 C10 C9 . . 120.0(2) ?
C11 C10 H10A . . 120.0 ?
C9 C10 H10A . . 120.0 ?
C10 C11 C12 . . 119.8(2) ?
C10 C11 N2 . . 116.9(2) ?
C12 C11 N2 . . 123.3(2) ?
C13 C12 C11 . . 121.5(2) ?
C13 C12 H12A . . 119.2 ?
C11 C12 H12A . . 119.2 ?
C12 C13 C14 . . 118.2(2) ?
C12 C13 H13A . . 120.9 ?
C14 C13 H13A . . 120.9 ?
N1 C14 C13 . . 129.8(2) ?
N1 C14 C9 . . 108.9(2) ?
C13 C14 C9 . . 121.3(2) ?
N2 C15 C16 . . 122.9(3) ?
N2 C15 H15A . . 118.5 ?
C16 C15 H15A . . 118.5 ?
C17 C16 C21 . . 117.5(3) ?
C17 C16 C15 . . 120.8(3) ?
C21 C16 C15 . . 121.6(3) ?
C16 C17 C18 . . 121.3(3) ?
C16 C17 H17A . . 119.4 ?
C18 C17 H17A . . 119.4 ?
C19 C18 C17 . . 119.7(3) ?
C19 C18 H18A . . 120.2 ?
C17 C18 H18A . . 120.2 ?
O1 C19 C18 . . 117.3(3) ?
O1 C19 C20 . . 122.6(3) ?
C18 C19 C20 . . 120.0(3) ?
C21 C20 C19 . . 119.5(3) ?
C21 C20 H20A . . 120.2 ?
C19 C20 H20A . . 120.2 ?
C20 C21 C16 . . 122.0(3) ?
C20 C21 H21A . . 119.0 ?
C16 C21 H21A . . 119.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C19 . 1.358(3) ?
O1 H1 . 0.8200 ?
N1 C14 . 1.377(3) ?
N1 C3 . 1.389(3) ?
N1 C2 . 1.457(3) ?
N2 C15 . 1.288(3) ?
N2 C11 . 1.418(3) ?
C1 C2 . 1.500(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 H2B . 0.9700 ?
C2 H2C . 0.9700 ?
C3 C4 . 1.379(3) ?
C3 C8 . 1.403(3) ?
C4 C5 . 1.366(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.380(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.371(4) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.390(3) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.435(3) ?
C9 C10 . 1.390(3) ?
C9 C14 . 1.407(3) ?
C10 C11 . 1.382(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.401(3) ?
C12 C13 . 1.376(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.392(3) ?
C13 H13A . 0.9300 ?
C15 C16 . 1.459(4) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.384(4) ?
C16 C21 . 1.385(4) ?
C17 C18 . 1.389(4) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.376(4) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.378(4) ?
C20 C21 . 1.377(4) ?
C20 H20A . 0.9300 ?
C21 H21A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N2 3_656 0.82 2.09 2.842(3) 153 y
C1 H1A Cg2 8_755 0.96 2.77 3.698(2) 162 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656393
