#------------------------------------------------------------------------------
#$Date: 2020-03-28 04:41:31 +0200 (Sat, 28 Mar 2020) $
#$Revision: 249813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240224.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_7240224
loop_
_publ_author_name
'Kilinkissa, Ornella E. Y.'
'Govender, Krishna Kuben'
'Bathori, Nikoletta B.'
_publ_section_title
;
 Melting point--solubility--structure correlations in chiral and racemic
 model cocrystals
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00014K
_journal_year                    2020
_chemical_formula_sum            'C15 H16 N O2'
_chemical_formula_weight         242.29
_chemical_melting_point          82.2(18)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2019-12-29 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.74(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6951(11)
_cell_length_b                   32.968(7)
_cell_length_c                   7.2241(14)
_cell_measurement_reflns_used    10554
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.255
_cell_measurement_theta_min      2.471
_cell_volume                     1276.7(5)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Duo Apex II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10554
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.255
_diffrn_reflns_theta_min         2.471
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0626
_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/[σ²(Fo²)+(0.0358P)²+1.0060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2470
_reflns_number_total             3116
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00014k2.cif
_cod_data_source_block           BIPYracPBA
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '80.5-84.0' was changed to
'82.2(18)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240224
_shelx_shelxl_version_number     2016/4
_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   0.988
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O3 O 0.8775(3) 0.09990(5) 0.1813(2) 0.0418(4) Uani 1 1 d . . . . .
H3 H 0.874463 0.081803 0.098659 0.050 Uiso 1 1 calc R U . . .
N1 N 0.9001(3) 0.05304(5) -0.1047(2) 0.0336(4) Uani 1 1 d . . . . .
O2 O 0.5478(3) 0.06647(5) 0.2003(2) 0.0451(4) Uani 1 1 d . . . . .
C6 C 0.5718(4) 0.16688(6) 0.2433(3) 0.0314(4) Uani 1 1 d . . . . .
C3 C 0.9784(3) 0.01103(5) -0.4172(3) 0.0270(4) Uani 1 1 d . . . . .
C5 C 0.7743(4) 0.01922(6) -0.1781(3) 0.0330(4) Uani 1 1 d . . . . .
H5 H 0.655509 0.009586 -0.122585 0.040 Uiso 1 1 calc R U . . .
C15 C 0.6876(4) 0.09500(6) 0.2432(3) 0.0306(4) Uani 1 1 d . . . . .
C2 C 1.1091(4) 0.04640(6) -0.3399(3) 0.0347(4) Uani 1 1 d . . . . .
H2 H 1.227546 0.056995 -0.393343 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8080(4) -0.00254(6) -0.3311(3) 0.0306(4) Uani 1 1 d . . . . .
H4 H 0.715209 -0.026646 -0.377135 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3223(4) 0.17052(6) 0.1268(3) 0.0354(5) Uani 1 1 d . . . . .
H7 H 0.205844 0.150501 0.134339 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6708(4) 0.13014(6) 0.3766(3) 0.0320(4) Uani 1 1 d . . . . .
H12 H 0.843513 0.136596 0.465913 0.038 Uiso 1 1 calc R U . . .
C1 C 1.0659(4) 0.06598(6) -0.1855(3) 0.0370(5) Uani 1 1 d . . . . .
H1 H 1.158635 0.089830 -0.134173 0.044 Uiso 1 1 calc R U . . .
C10 C 0.6550(5) 0.22910(6) 0.1012(3) 0.0420(5) Uani 1 1 d . . . . .
H10 H 0.770761 0.249247 0.093723 0.050 Uiso 1 1 calc R U . . .
C13 C 0.5149(4) 0.11877(6) 0.5034(3) 0.0387(5) Uani 1 1 d . . . . .
H13B H 0.339008 0.115296 0.417922 0.046 Uiso 1 1 calc R U . . .
H13A H 0.574197 0.092443 0.568339 0.046 Uiso 1 1 calc R U . . .
C8 C 0.2415(4) 0.20323(7) -0.0009(3) 0.0397(5) Uani 1 1 d . . . . .
H8 H 0.070350 0.205499 -0.078894 0.048 Uiso 1 1 calc R U . . .
C11 C 0.7368(4) 0.19665(6) 0.2293(3) 0.0369(5) Uani 1 1 d . . . . .
H11 H 0.907876 0.194832 0.308289 0.044 Uiso 1 1 calc R U . . .
C9 C 0.4091(5) 0.23246(6) -0.0148(3) 0.0414(5) Uani 1 1 d . . . . .
H9 H 0.354679 0.254556 -0.103451 0.050 Uiso 1 1 calc R U . . .
C14 C 0.5272(6) 0.15019(8) 0.6590(4) 0.0562(7) Uani 1 1 d . . . . .
H14A H 0.699827 0.152921 0.747784 0.084 Uiso 1 1 calc R U . . .
H14B H 0.421136 0.141680 0.734233 0.084 Uiso 1 1 calc R U . . .
H14C H 0.468446 0.176342 0.595770 0.084 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 117.18(17) . . ?
C11 C6 C7 118.31(19) . . ?
C11 C6 C12 119.41(19) . . ?
C7 C6 C12 122.20(18) . . ?
C4 C3 C2 116.62(17) . . ?
C4 C3 C3 122.1(2) . 3_754 ?
C2 C3 C3 121.3(2) . 3_754 ?
N1 C5 C4 123.33(18) . . ?
O2 C15 O3 123.95(18) . . ?
O2 C15 C12 125.23(18) . . ?
O3 C15 C12 110.82(16) . . ?
C1 C2 C3 119.87(18) . . ?
C5 C4 C3 119.74(18) . . ?
C6 C7 C8 120.59(19) . . ?
C13 C12 C15 111.46(16) . . ?
C13 C12 C6 114.03(16) . . ?
C15 C12 C6 106.90(15) . . ?
N1 C1 C2 123.25(19) . . ?
C9 C10 C11 120.9(2) . . ?
C14 C13 C12 112.86(18) . . ?
C9 C8 C7 120.4(2) . . ?
C6 C11 C10 120.7(2) . . ?
C10 C9 C8 119.1(2) . . ?
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
O3 C15 1.312(2) . ?
N1 C5 1.335(3) . ?
N1 C1 1.337(3) . ?
O2 C15 1.203(2) . ?
C6 C11 1.386(3) . ?
C6 C7 1.391(3) . ?
C6 C12 1.532(3) . ?
C3 C4 1.392(2) . ?
C3 C2 1.395(3) . ?
C3 C3 1.489(4) 3_754 ?
C5 C4 1.384(3) . ?
C15 C12 1.531(3) . ?
C2 C1 1.381(3) . ?
C7 C8 1.392(3) . ?
C12 C13 1.523(3) . ?
C10 C9 1.372(3) . ?
C10 C11 1.388(3) . ?
C13 C14 1.513(3) . ?
C8 C9 1.384(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 N1 0.84 1.80 2.618(2) 165.6 .
C4 H4 O2_$1 0.95 2.63 3.276(2) 126.1 3_655
C5 H5 O2_$1 0.95 2.74 3.342(3) 122.1 3_655
C5 H5 O2 0.95 3.21 3.735(3) 116.7 .
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
C1 N1 C5 C4 0.1(3) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C3 C3 C2 C1 -179.6(2) 3_754 . . . ?
N1 C5 C4 C3 -0.8(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C3 C4 C5 -179.7(2) 3_754 . . . ?
C11 C6 C7 C8 0.2(3) . . . . ?
C12 C6 C7 C8 -176.37(17) . . . . ?
O2 C15 C12 C13 19.1(3) . . . . ?
O3 C15 C12 C13 -160.61(18) . . . . ?
O2 C15 C12 C6 -106.2(2) . . . . ?
O3 C15 C12 C6 74.2(2) . . . . ?
C11 C6 C12 C13 135.34(19) . . . . ?
C7 C6 C12 C13 -48.1(3) . . . . ?
C11 C6 C12 C15 -101.0(2) . . . . ?
C7 C6 C12 C15 75.5(2) . . . . ?
C5 N1 C1 C2 0.7(3) . . . . ?
C3 C2 C1 N1 -0.8(3) . . . . ?
C15 C12 C13 C14 171.05(19) . . . . ?
C6 C12 C13 C14 -67.8(3) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C7 C6 C11 C10 -0.4(3) . . . . ?
C12 C6 C11 C10 176.25(18) . . . . ?
C9 C10 C11 C6 -0.1(3) . . . . ?
C11 C10 C9 C8 0.8(3) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
