#------------------------------------------------------------------------------
#$Date: 2020-04-21 01:36:04 +0200 (mar 21 de abr de 2020) $
#$Revision: 250963 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/03/7240347.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_7240347
loop_
_publ_author_name
'Pereira Copetti, João Pedro'
'Salbego, Paulo Roberto dos Santos'
'Orlando, Tainára'
'Rosa, Jéssica Maria Luis'
'Fiss, Gabriela Fehn'
'Gomes de Oliveira, João Paulo'
'de Almeida Vasconcellos, Mário Luiz Araújo'
'Zanatta, Nilo'
'Bonacorso, Helio Gauze'
'Martins, Marcos A. P.'
_publ_section_title
;
 Substituent Effects in the Crystallization Mechanisms of
 7-chloro-4-substituted-Quinolines
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00214C
_journal_year                    2020
_chemical_formula_moiety         'C11 H11 Cl N2 O'
_chemical_formula_sum            'C11 H11 Cl N2 O'
_chemical_formula_weight         222.67
_chemical_melting_point          ?
_chemical_name_common            aminoquinolina
_chemical_name_systematic        2-((7-chloroquinolin-4-yl)amino)ethanol
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-10 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.5838(2)
_cell_length_b                   14.8986(7)
_cell_length_c                   14.9416(7)
_cell_measurement_reflns_used    5230
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.0715
_cell_measurement_theta_min      2.4115
_cell_volume                     1018.51(8)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14860
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         21.086
_diffrn_reflns_theta_min         2.410
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption 
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & 
Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0658P)²+0.2462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1898
_reflns_number_total             2235
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00214c2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'none' was changed to '?'
-- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7240347
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.908
_shelx_estimated_absorpt_t_max   0.971
_exptl_absorpt_special_details   none
loop_
_space_group_symop_operation_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_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
Cl1 Cl 1.08492(8) 0.40501(3) 0.92348(3) 0.02094(14) Uani 1 1 d . . . . .
O1 O -0.0261(2) 0.44708(7) 0.40305(7) 0.0157(2) Uani 1 1 d . . . . .
H1 H 0.033621 0.409767 0.368203 0.024 Uiso 1 1 calc R U . . .
N51 N 0.0712(3) 0.35393(8) 0.57680(8) 0.0140(3) Uani 1 1 d . . . . .
H51 H 0.119655 0.409570 0.581530 0.017 Uiso 1 1 calc R U . . .
N1 N 0.4719(3) 0.16728(9) 0.75696(9) 0.0176(3) Uani 1 1 d . . . . .
C8 C 0.8315(3) 0.37200(11) 0.83833(10) 0.0147(3) Uani 1 1 d . . . . .
C9 C 0.7533(3) 0.28380(10) 0.83011(10) 0.0150(3) Uani 1 1 d . . . . .
H9 H 0.838362 0.241350 0.869170 0.018 Uiso 1 1 calc R U . . .
C10 C 0.5425(3) 0.25698(10) 0.76205(10) 0.0137(3) Uani 1 1 d . . . . .
C5 C 0.4152(3) 0.32266(10) 0.70319(10) 0.0126(3) Uani 1 1 d . . . . .
C4 C 0.2010(3) 0.29372(10) 0.63409(10) 0.0130(3) Uani 1 1 d . . . . .
C52 C -0.1484(3) 0.32716(10) 0.50728(10) 0.0143(3) Uani 1 1 d . . . . .
H52A H -0.313623 0.300096 0.534654 0.017 Uiso 1 1 calc R U . . .
H52B H -0.066247 0.282915 0.468383 0.017 Uiso 1 1 calc R U . . .
C53 C -0.2502(3) 0.40823(10) 0.45255(10) 0.0153(3) Uani 1 1 d . . . . .
H53A H -0.411136 0.390514 0.411165 0.018 Uiso 1 1 calc R U . . .
H53B H -0.322756 0.453223 0.492527 0.018 Uiso 1 1 calc R U . . .
C2 C 0.2813(3) 0.14390(10) 0.69095(11) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.235029 0.083268 0.685737 0.022 Uiso 1 1 calc R U . . .
C3 C 0.1435(3) 0.20199(10) 0.62848(10) 0.0159(3) Uani 1 1 d . . . . .
H3 H 0.014301 0.179667 0.583476 0.019 Uiso 1 1 calc R U . . .
C6 C 0.5070(3) 0.41296(10) 0.71341(10) 0.0154(3) Uani 1 1 d . . . . .
H6 H 0.426774 0.456279 0.674428 0.018 Uiso 1 1 calc R U . . .
C7 C 0.7116(3) 0.43807(10) 0.77953(10) 0.0154(3) Uani 1 1 d . . . . .
H7 H 0.770152 0.497660 0.785419 0.018 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.0998 0.0984 '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
_geom_angle_publ_flag
C53 O1 H1 109.5 . . ?
C4 N51 C52 121.86(13) . . ?
C4 N51 H51 119.1 . . ?
C52 N51 H51 119.1 . . ?
C2 N1 C10 116.04(13) . . ?
C9 C8 C7 121.74(14) . . ?
C9 C8 Cl1 119.83(12) . . ?
C7 C8 Cl1 118.43(12) . . ?
C8 C9 C10 119.98(14) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
N1 C10 C9 117.47(13) . . ?
N1 C10 C5 123.35(13) . . ?
C9 C10 C5 119.18(14) . . ?
C6 C5 C10 118.75(13) . . ?
C6 C5 C4 123.01(13) . . ?
C10 C5 C4 118.23(13) . . ?
N51 C4 C3 122.54(14) . . ?
N51 C4 C5 120.49(13) . . ?
C3 C4 C5 116.94(14) . . ?
N51 C52 C53 110.06(12) . . ?
N51 C52 H52A 109.6 . . ?
C53 C52 H52A 109.6 . . ?
N51 C52 H52B 109.6 . . ?
C53 C52 H52B 109.6 . . ?
H52A C52 H52B 108.2 . . ?
O1 C53 C52 113.32(12) . . ?
O1 C53 H53A 108.9 . . ?
C52 C53 H53A 108.9 . . ?
O1 C53 H53B 108.9 . . ?
C52 C53 H53B 108.9 . . ?
H53A C53 H53B 107.7 . . ?
N1 C2 C3 125.91(14) . . ?
N1 C2 H2 117.0 . . ?
C3 C2 H2 117.0 . . ?
C4 C3 C2 119.45(14) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C7 C6 C5 121.50(14) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 118.82(14) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.7408(15) . ?
O1 C53 1.4245(19) . ?
O1 H1 0.8200 . ?
N51 C4 1.3526(19) . ?
N51 C52 1.4577(18) . ?
N51 H51 0.8600 . ?
N1 C2 1.324(2) . ?
N1 C10 1.376(2) . ?
C8 C9 1.366(2) . ?
C8 C7 1.409(2) . ?
C9 C10 1.417(2) . ?
C9 H9 0.9300 . ?
C10 C5 1.417(2) . ?
C5 C6 1.415(2) . ?
C5 C4 1.447(2) . ?
C4 C3 1.393(2) . ?
C52 C53 1.516(2) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C2 C3 1.396(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C6 C7 1.372(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
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
_geom_torsion_publ_flag
C7 C8 C9 C10 -1.1(2) . . . . ?
Cl1 C8 C9 C10 178.66(11) . . . . ?
C2 N1 C10 C9 -177.94(13) . . . . ?
C2 N1 C10 C5 2.1(2) . . . . ?
C8 C9 C10 N1 -179.94(14) . . . . ?
C8 C9 C10 C5 0.0(2) . . . . ?
N1 C10 C5 C6 -179.00(14) . . . . ?
C9 C10 C5 C6 1.1(2) . . . . ?
N1 C10 C5 C4 -0.2(2) . . . . ?
C9 C10 C5 C4 179.86(13) . . . . ?
C52 N51 C4 C3 2.7(2) . . . . ?
C52 N51 C4 C5 -179.11(12) . . . . ?
C6 C5 C4 N51 -1.9(2) . . . . ?
C10 C5 C4 N51 179.37(13) . . . . ?
C6 C5 C4 C3 176.37(14) . . . . ?
C10 C5 C4 C3 -2.4(2) . . . . ?
C4 N51 C52 C53 -178.94(13) . . . . ?
N51 C52 C53 O1 64.93(16) . . . . ?
C10 N1 C2 C3 -1.5(2) . . . . ?
N51 C4 C3 C2 -178.79(14) . . . . ?
C5 C4 C3 C2 3.0(2) . . . . ?
N1 C2 C3 C4 -1.1(2) . . . . ?
C10 C5 C6 C7 -1.0(2) . . . . ?
C4 C5 C6 C7 -179.75(14) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C9 C8 C7 C6 1.2(2) . . . . ?
Cl1 C8 C7 C6 -178.60(12) . . . . ?
