Substituent Effects in the Crystallization Mechanisms of 7-chloro-4-substituted-Quinolines
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.; CrystEngComm  (2020) –; doi:10.1039/D0CE00214C

data_7240346
_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_absolute_configuration none
_chemical_formula_moiety         'C11 H10 Cl N O2'
_chemical_formula_sum            'C11 H10 Cl N O2'
_chemical_formula_weight         223.65
_chemical_melting_point          ?
_chemical_name_common            2-((7-chloroquinolin-4-yl)oxy)ethan-1-ol
_chemical_name_systematic        2-((7-chloroquinolin-4-yl)oxy)ethan-1-ol
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 102.074(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.3139(2)
_cell_length_b                   25.5732(14)
_cell_length_c                   9.5710(5)
_cell_measurement_reflns_used    6819
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      2.32
_cell_volume                     1032.52(9)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon 100 diffractometer'
_diffrn_measurement_method       '2\%\f & \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.996
_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       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17777
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.128
_diffrn_reflns_theta_min         2.317
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1410 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4540
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0411
_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/[\s^2^(Fo^2^)+(0.0389P)^2^+0.1493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3560
_reflns_number_total             4540
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00214c2.cif
_cod_data_source_block           shelx_CCDC1
_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'
_cod_database_code               7240346
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.982
_exptl_absorpt_special_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
absortion correction based on the indexed faces of the crystal.
;
_shelx_res_checksum              219
_shelx_hkl_checksum              80014