#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/35/1553567.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_1553567
loop_
_publ_author_name
'Zhu, Chao-Qun'
'Deng, Zhuo-Fei'
'Zhang, Yahong'
'Wang, You-Qing'
_publ_section_title
;
 Synthesis of 4-substituted 3-(2-hydroxyphenyl)-quinolines through an
 unexpected iron(iii) chloride promoted reaction of cyclic imine
 dibenzo[b,f][1,4]oxazepines with alkynes
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              196
_journal_paper_doi               10.1039/C6QO00545D
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C22 H16 Cl N O2'
_chemical_formula_weight         361.81
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-05-26 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.536(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.366(4)
_cell_length_b                   11.305(4)
_cell_length_c                   14.788(6)
_cell_measurement_reflns_used    3621
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.33
_cell_volume                     1779.4(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8874
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9553
_exptl_absorpt_correction_T_min  0.8741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0359
_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)+(0.0808P)²+0.1750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                2489
_reflns_number_total             3130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00545d2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               1553567
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl Cl 0.35125(5) 0.52820(5) -0.00275(5) 0.0823(2) Uani 1 1 d .
N1 N -0.11578(12) 0.60727(12) -0.14405(10) 0.0470(3) Uani 1 1 d .
C1 C 0.21577(16) 0.59508(16) 0.00091(14) 0.0533(4) Uani 1 1 d .
C2 C 0.22541(16) 0.67506(18) 0.07486(14) 0.0584(5) Uani 1 1 d .
H2B H 0.3029 0.6899 0.1225 0.070 Uiso 1 1 calc R
C3 C 0.10406(16) 0.57018(14) -0.06893(13) 0.0492(4) Uani 1 1 d .
H3A H 0.0996 0.5145 -0.1163 0.059 Uiso 1 1 calc R
C4 C 0.12013(15) 0.73136(16) 0.07674(12) 0.0510(4) Uani 1 1 d .
H4A H 0.1265 0.7839 0.1266 0.061 Uiso 1 1 calc R
C5 C -0.00567(14) 0.62933(13) -0.06925(11) 0.0404(4) Uani 1 1 d .
C6 C 0.00145(14) 0.71145(13) 0.00433(11) 0.0390(3) Uani 1 1 d .
C9 C -0.21481(15) 0.66804(14) -0.14583(11) 0.0453(4) Uani 1 1 d .
H9A H -0.2895 0.6534 -0.1966 0.054 Uiso 1 1 calc R
C10 C -0.21787(14) 0.75359(13) -0.07748(10) 0.0380(3) Uani 1 1 d .
C12 C -0.33811(13) 0.81733(13) -0.09198(10) 0.0395(4) Uani 1 1 d .
C13 C -0.37442(15) 0.90960(14) -0.15807(11) 0.0437(4) Uani 1 1 d .
C14 C -0.41574(16) 0.78657(15) -0.04186(12) 0.0507(4) Uani 1 1 d .
H14A H -0.3923 0.7249 0.0025 0.061 Uiso 1 1 calc R
C15 C -0.48564(16) 0.97049(16) -0.17047(13) 0.0542(4) Uani 1 1 d .
H15A H -0.5088 1.0339 -0.2131 0.065 Uiso 1 1 calc R
C16 C -0.52697(18) 0.84510(17) -0.05596(15) 0.0622(5) Uani 1 1 d .
H16A H -0.5786 0.8222 -0.0222 0.075 Uiso 1 1 calc R
C17 C -0.10933(14) 0.77454(13) 0.00000(10) 0.0372(3) Uani 1 1 d .
C18 C -0.10508(13) 0.86292(13) 0.07548(10) 0.0384(3) Uani 1 1 d .
C19 C -0.08611(17) 0.82979(15) 0.16979(12) 0.0510(4) Uani 1 1 d .
H19A H -0.0751 0.7502 0.1866 0.061 Uiso 1 1 calc R
C20 C -0.12083(15) 0.98217(14) 0.05316(11) 0.0416(4) Uani 1 1 d .
H20A H -0.1346 1.0064 -0.0098 0.050 Uiso 1 1 calc R
C21 C -0.08323(18) 0.91202(16) 0.23913(12) 0.0550(5) Uani 1 1 d .
H21A H -0.0709 0.8877 0.3019 0.066 Uiso 1 1 calc R
C22 C -0.09871(16) 1.03078(15) 0.21549(11) 0.0474(4) Uani 1 1 d .
C23 C -0.11662(16) 1.06611(14) 0.12225(12) 0.0458(4) Uani 1 1 d .
H23A H -0.1258 1.1459 0.1060 0.055 Uiso 1 1 calc R
C24 C -0.1163(3) 1.2265(2) 0.26709(17) 0.0901(8) Uani 1 1 d .
H24A H -0.1120 1.2688 0.3245 0.135 Uiso 1 1 calc R
H24B H -0.1977 1.2376 0.2185 0.135 Uiso 1 1 calc R
H24C H -0.0529 1.2558 0.2438 0.135 Uiso 1 1 calc R
C25 C -0.56104(17) 0.93730(17) -0.12004(14) 0.0593(5) Uani 1 1 d .
H25A H -0.6357 0.9776 -0.1294 0.071 Uiso 1 1 calc R
O1 O -0.09629(15) 1.10578(12) 0.28831(9) 0.0727(4) Uani 1 1 d .
O2 O -0.29716(13) 0.93864(13) -0.20661(10) 0.0671(4) Uani 1 1 d .
H2 H -0.3296(11) 0.997(2) -0.2457(13) 0.101 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
C9 N1 C5 117.06(13)
C3 C1 C2 121.83(15)
C3 C1 Cl 119.37(15)
C2 C1 Cl 118.78(14)
C4 C2 C1 119.38(16)
C4 C2 H2B 120.3
C1 C2 H2B 120.3
C1 C3 C5 119.58(16)
C1 C3 H3A 120.2
C5 C3 H3A 120.2
C2 C4 C6 121.35(17)
C2 C4 H4A 119.3
C6 C4 H4A 119.3
N1 C5 C6 122.08(13)
N1 C5 C3 118.10(14)
C6 C5 C3 119.79(14)
C5 C6 C4 118.02(14)
C5 C6 C17 118.86(14)
C4 C6 C17 123.05(14)
N1 C9 C10 125.64(14)
N1 C9 H9A 117.2
C10 C9 H9A 117.2
C17 C10 C9 118.33(14)
C17 C10 C12 122.96(13)
C9 C10 C12 118.71(13)
C14 C12 C13 118.58(14)
C14 C12 C10 121.76(14)
C13 C12 C10 119.65(13)
O2 C13 C12 117.82(14)
O2 C13 C15 122.47(15)
C12 C13 C15 119.69(15)
C16 C14 C12 121.56(16)
C16 C14 H14A 119.2
C12 C14 H14A 119.2
C25 C15 C13 120.29(16)
C25 C15 H15A 119.9
C13 C15 H15A 119.9
C25 C16 C14 119.49(17)
C25 C16 H16A 120.3
C14 C16 H16A 120.3
C10 C17 C6 117.98(14)
C10 C17 C18 121.58(13)
C6 C17 C18 120.40(13)
C20 C18 C19 117.67(14)
C20 C18 C17 120.55(13)
C19 C18 C17 121.78(14)
C21 C19 C18 121.47(16)
C21 C19 H19A 119.3
C18 C19 H19A 119.3
C18 C20 C23 121.60(14)
C18 C20 H20A 119.2
C23 C20 H20A 119.2
C19 C21 C22 119.99(15)
C19 C21 H21A 120.0
C22 C21 H21A 120.0
O1 C22 C23 124.34(16)
O1 C22 C21 116.01(15)
C23 C22 C21 119.64(15)
C20 C23 C22 119.62(15)
C20 C23 H23A 120.2
C22 C23 H23A 120.2
O1 C24 H24A 109.5
O1 C24 H24B 109.5
H24A C24 H24B 109.5
O1 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C16 C25 C15 120.37(16)
C16 C25 H25A 119.8
C15 C25 H25A 119.8
C22 O1 C24 118.17(15)
C13 O2 H2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl C1 1.7332(17)
N1 C9 1.311(2)
N1 C5 1.371(2)
C1 C3 1.356(3)
C1 C2 1.393(3)
C2 C4 1.364(2)
C2 H2B 0.9300
C3 C5 1.414(2)
C3 H3A 0.9300
C4 C6 1.415(2)
C4 H4A 0.9300
C5 C6 1.411(2)
C6 C17 1.429(2)
C9 C10 1.408(2)
C9 H9A 0.9300
C10 C17 1.378(2)
C10 C12 1.492(2)
C12 C14 1.381(2)
C12 C13 1.389(2)
C13 O2 1.355(2)
C13 C15 1.394(2)
C14 C16 1.376(2)
C14 H14A 0.9300
C15 C25 1.371(3)
C15 H15A 0.9300
C16 C25 1.370(3)
C16 H16A 0.9300
C17 C18 1.486(2)
C18 C20 1.385(2)
C18 C19 1.386(2)
C19 C21 1.376(2)
C19 H19A 0.9300
C20 C23 1.383(2)
C20 H20A 0.9300
C21 C22 1.383(3)
C21 H21A 0.9300
C22 O1 1.363(2)
C22 C23 1.380(2)
C23 H23A 0.9300
C24 O1 1.401(3)
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
C25 H25A 0.9300
O2 H2 0.8729
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 141463641
