#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/81/1558199.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_1558199
loop_
_publ_author_name
'Ding, Xiaodan'
'Unruh, Daniel K.'
'Groeneman , Ryan'
'Hutchins, Kristin M.'
_publ_section_title
;
 Controlling thermal expansion within mixed cocrystals by tuning molecular
 motion capability
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02795B
_journal_year                    2020
_chemical_formula_sum            'C18 H14.61 N2 O2'
_chemical_formula_weight         290.92
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-04-02T10:30:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                92.130(3)
_cell_angle_beta                 108.187(2)
_cell_angle_gamma                114.618(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1603(2)
_cell_length_b                   9.8060(3)
_cell_length_c                   10.9374(2)
_cell_measurement_reflns_used    10959
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      77.022
_cell_measurement_theta_min      4.319
_cell_volume                     741.61(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1332736
_diffrn_orient_matrix_UB_12      0.0490232
_diffrn_orient_matrix_UB_13      0.0354945
_diffrn_orient_matrix_UB_21      -0.0519622
_diffrn_orient_matrix_UB_22      -0.0757116
_diffrn_orient_matrix_UB_23      0.1444376
_diffrn_orient_matrix_UB_31      0.1573572
_diffrn_orient_matrix_UB_32      -0.1512967
_diffrn_orient_matrix_UB_33      -0.0267242
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14653
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.439
_diffrn_reflns_theta_min         4.337
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.94947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       irregular
_exptl_crystal_F_000             305
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.03
_refine_ls_extinction_coef       0.0035(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     438
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0469P)²+0.0813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0
_reflns_number_gt                2817
_reflns_number_total             3073
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE25_BA75_190
_cod_database_code               1558199
_shelx_estimated_absorpt_t_min   0.868
_shelx_estimated_absorpt_t_max   0.945
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.16673(10) 0.14786(8) 0.30455(7) 0.04067(18) Uani 1 1 d . . . . .
H1 H 0.200554 0.173878 0.385988 0.061 Uiso 1 1 calc R U . . .
O2 O 0.81959(10) 0.21562(9) 0.43371(7) 0.0469(2) Uani 1 1 d . . . . .
H2A H 0.825512 0.253007 0.506229 0.07 Uiso 1 1 calc R U . . .
N1 N 0.26298(12) 0.24298(10) -0.43254(8) 0.0421(2) Uani 1 1 d . . . . .
C1 C 0.31724(13) 0.14750(9) 0.27613(9) 0.0340(2) Uani 1 1 d . . . . .
C2 C 0.49284(13) 0.18068(10) 0.37405(8) 0.0340(2) Uani 1 1 d . . . . .
H2 H 0.509381 0.203722 0.46352 0.041 Uiso 1 1 calc R U . . .
C3 C 0.64473(14) 0.18026(10) 0.34139(9) 0.0365(2) Uani 1 1 d . . . . .
C4 C 0.61958(16) 0.14323(11) 0.21045(10) 0.0431(2) Uani 1 1 d . . . . .
H4 H 0.721459 0.14066 0.187453 0.052 Uiso 1 1 calc R U . . .
C5 C 0.44376(17) 0.11028(12) 0.11450(10) 0.0463(3) Uani 1 1 d . . . . .
H5 H 0.426406 0.085572 0.025084 0.056 Uiso 1 1 calc R U . . .
C6 C 0.29209(15) 0.11229(11) 0.14510(9) 0.0417(2) Uani 1 1 d . . . . .
H6 H 0.172776 0.089945 0.07761 0.05 Uiso 1 1 calc R U . . .
C7 C 0.19766(14) 0.14688(11) -0.35647(10) 0.0406(2) Uani 1 1 d . . . . .
H7 H 0.153691 0.040852 -0.385071 0.049 Uiso 1 1 calc R U . . .
C8 C 0.19070(14) 0.19362(11) -0.23835(9) 0.0387(2) Uani 1 1 d . . . . .
H8 H 0.141652 0.120908 -0.187895 0.046 Uiso 1 1 calc R U . . .
C9 C 0.25652(13) 0.34873(11) -0.19417(9) 0.0356(2) Uani 1 1 d D . . . .
C10 C 0.32989(15) 0.44984(11) -0.27135(10) 0.0413(2) Uani 1 1 d . . . . .
H10 H 0.379981 0.556908 -0.243716 0.05 Uiso 1 1 calc R U . . .
C11 C 0.32855(15) 0.39191(12) -0.38844(10) 0.0439(2) Uani 1 1 d . . . . .
H11 H 0.37707 0.46186 -0.440978 0.053 Uiso 1 1 calc R U . . .
C12 C 0.2193(17) 0.3803(10) -0.0671(11) 0.0287(13) Uani 0.303(10) 1 d D U P A 1
H12 H 0.160509 0.296269 -0.029079 0.034 Uiso 0.303(10) 1 calc R U P A 1
C13 C 0.2655(7) 0.5177(8) -0.0107(5) 0.0300(11) Uani 0.303(10) 1 d D U P A 1
H13 H 0.329462 0.599223 -0.049097 0.036 Uiso 0.303(10) 1 calc R U P A 1
C14A C 0.2287(18) 0.5624(12) 0.1099(9) 0.0307(17) Uani 0.303(10) 1 d DG U P A 1
C15A C 0.1474(18) 0.4509(9) 0.1770(10) 0.0352(18) Uani 0.303(10) 1 d G U P A 1
H15A H 0.11466 0.34725 0.14768 0.042 Uiso 0.303(10) 1 calc R U P A 1
C16A C 0.1141(18) 0.4910(12) 0.2869(10) 0.0344(19) Uani 0.303(10) 1 d G U P A 1
H16A H 0.058622 0.414754 0.33276 0.041 Uiso 0.303(10) 1 calc R U P A 1
N2A N 0.162(2) 0.6426(13) 0.3298(10) 0.0308(17) Uani 0.303(10) 1 d G U P A 1
C17A C 0.243(2) 0.7541(10) 0.2628(12) 0.0347(19) Uani 0.303(10) 1 d G U P A 1
H17A H 0.276121 0.85768 0.292083 0.042 Uiso 0.303(10) 1 calc R U P A 1
C18A C 0.2766(19) 0.7140(11) 0.1528(11) 0.0333(17) Uani 0.303(10) 1 d G U P A 1
H18A H 0.332162 0.790179 0.107002 0.04 Uiso 0.303(10) 1 calc R U P A 1
C14B C 0.2158(8) 0.5289(6) 0.1227(4) 0.0338(8) Uani 0.697(10) 1 d D U P A 2
C15B C 0.1265(8) 0.4423(5) 0.2022(5) 0.0378(7) Uani 0.697(10) 1 d . U P A 2
H15B H 0.07741 0.334214 0.185991 0.045 Uiso 0.697(10) 1 calc R U P A 2
C16B C 0.1104(8) 0.5156(6) 0.3047(5) 0.0374(8) Uani 0.697(10) 1 d . U P A 2
H16B H 0.047536 0.454249 0.356903 0.045 Uiso 0.697(10) 1 calc R U P A 2
N2B N 0.1761(9) 0.6654(6) 0.3355(5) 0.0395(9) Uani 0.697(10) 1 d . U P A 2
C17B C 0.2604(9) 0.7453(5) 0.2592(6) 0.0397(9) Uani 0.697(10) 1 d . U P A 2
H17B H 0.309495 0.853166 0.279153 0.048 Uiso 0.697(10) 1 calc R U P A 2
C18B C 0.2831(8) 0.6859(6) 0.1536(5) 0.0357(8) Uani 0.697(10) 1 d . U P A 2
H18B H 0.343905 0.75115 0.102486 0.043 Uiso 0.697(10) 1 calc R U P A 2
C19 C 0.2519(8) 0.4118(6) -0.0792(5) 0.0381(8) Uani 0.697(10) 1 d D U P A 2
C20 C 0.2348(4) 0.4630(5) 0.0148(3) 0.0388(6) Uani 0.697(10) 1 d D U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -4 -1 0.0431
-5 -1 -4 0.0754
-5 -4 0 0.0393
-1 4 5 0.0478
0 3 -5 0.0753
0 -3 -6 0.0824
5 5 0 0.0431
-2 4 2 0.0449
-2 -6 -1 0.0344
3 6 5 0.0681
-5 -1 1 0.0424
-3 1 4 0.0384
-3 -3 4 0.0674
3 3 -4 0.0729
1 0 7 0.0918
1 3 7 0.0812
-3 2 -5 0.0856
0 -6 -4 0.0552
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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C7 N1 C11 117.10(8) . . ?
O1 C1 C2 121.72(8) . . ?
O1 C1 C6 118.30(9) . . ?
C2 C1 C6 119.98(9) . . ?
C1 C2 C3 120.23(8) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 117.93(9) . . ?
O2 C3 C2 122.04(8) . . ?
C4 C3 C2 120.03(9) . . ?
C5 C4 C3 118.86(9) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.87(9) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.01(9) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.37(9) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.12(9) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 117.73(9) . . ?
C10 C9 C19 116.9(2) . . ?
C8 C9 C19 125.3(2) . . ?
C10 C9 C12 129.5(3) . . ?
C8 C9 C12 112.5(3) . . ?
C11 C10 C9 118.81(9) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.83(9) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 122.7(8) . . ?
C13 C12 H12 118.7 . . ?
C9 C12 H12 118.7 . . ?
C12 C13 C14A 127.5(8) . . ?
C12 C13 H13 116.2 . . ?
C14A C13 H13 116.2 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 119.8(5) . . ?
C18A C14A C13 120.2(5) . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
C15A C16A N2A 120 . . ?
C15A C16A H16A 120 . . ?
N2A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 116.52(19) . . ?
C18B C14B C20 120.8(3) . . ?
C15B C14B C20 122.7(3) . . ?
C16B C15B C14B 119.1(2) . . ?
C16B C15B H15B 120.5 . . ?
C14B C15B H15B 120.5 . . ?
N2B C16B C15B 124.7(2) . . ?
N2B C16B H16B 117.7 . . ?
C15B C16B H16B 117.7 . . ?
C17B N2B C16B 115.3(2) . . ?
N2B C17B C18B 125.6(2) . . ?
N2B C17B H17B 117.2 . . ?
C18B C17B H17B 117.2 . . ?
C17B C18B C14B 118.83(19) . . ?
C17B C18B H18B 120.6 . . ?
C14B C18B H18B 120.6 . . ?
C20 C19 C9 175.5(5) . . ?
C19 C20 C14B 177.4(5) . . ?
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
O1 C1 1.3590(11) . ?
O1 H1 0.84 . ?
O2 C3 1.3559(12) . ?
O2 H2A 0.84 . ?
N1 C7 1.3346(13) . ?
N1 C11 1.3369(14) . ?
C1 C2 1.3907(13) . ?
C1 C6 1.3913(13) . ?
C2 C3 1.3945(13) . ?
C2 H2 0.95 . ?
C3 C4 1.3931(13) . ?
C4 C5 1.3831(16) . ?
C4 H4 0.95 . ?
C5 C6 1.3866(15) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3804(13) . ?
C7 H7 0.95 . ?
C8 C9 1.3922(13) . ?
C8 H8 0.95 . ?
C9 C10 1.3918(14) . ?
C9 C19 1.399(5) . ?
C9 C12 1.559(10) . ?
C10 C11 1.3766(15) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.306(11) . ?
C12 H12 0.95 . ?
C13 C14A 1.529(8) . ?
C13 H13 0.95 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.95 . ?
C16A N2A 1.39 . ?
C16A H16A 0.95 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.95 . ?
C18A H18A 0.95 . ?
C14B C18B 1.388(3) . ?
C14B C15B 1.395(4) . ?
C14B C20 1.406(4) . ?
C15B C16B 1.379(4) . ?
C15B H15B 0.95 . ?
C16B N2B 1.323(3) . ?
C16B H16B 0.95 . ?
N2B C17B 1.319(3) . ?
C17B C18B 1.372(3) . ?
C17B H17B 0.95 . ?
C18B H18B 0.95 . ?
C19 C20 1.198(6) . ?
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
_geom_hbond_publ_flag
O1 H1 N1 0.84 1.91 2.7452(11) 174.6 1_556 yes
O2 H2A N2A^a 0.84 1.98 2.82(5) 174.7 2_666 yes
O2 H2A N2B^b 0.84 1.89 2.725(4) 176.7 2_666 yes
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
O1 C1 C2 C3 -179.59(8) . . . . ?
C6 C1 C2 C3 0.62(13) . . . . ?
C1 C2 C3 O2 178.36(8) . . . . ?
C1 C2 C3 C4 -1.41(14) . . . . ?
O2 C3 C4 C5 -178.51(9) . . . . ?
C2 C3 C4 C5 1.27(14) . . . . ?
C3 C4 C5 C6 -0.36(16) . . . . ?
C4 C5 C6 C1 -0.42(15) . . . . ?
O1 C1 C6 C5 -179.51(8) . . . . ?
C2 C1 C6 C5 0.29(14) . . . . ?
C11 N1 C7 C8 1.66(15) . . . . ?
N1 C7 C8 C9 -0.70(15) . . . . ?
C7 C8 C9 C10 -1.12(14) . . . . ?
C7 C8 C9 C19 177.6(3) . . . . ?
C7 C8 C9 C12 174.1(5) . . . . ?
C8 C9 C10 C11 1.91(14) . . . . ?
C19 C9 C10 C11 -176.9(3) . . . . ?
C12 C9 C10 C11 -172.4(6) . . . . ?
C7 N1 C11 C10 -0.79(15) . . . . ?
C9 C10 C11 N1 -1.00(15) . . . . ?
C10 C9 C12 C13 -3.8(14) . . . . ?
C8 C9 C12 C13 -178.4(8) . . . . ?
C9 C12 C13 C14A 177.1(8) . . . . ?
C12 C13 C14A C15A 4.2(12) . . . . ?
C12 C13 C14A C18A -175.9(9) . . . . ?
C18A C14A C15A C16A 0 . . . . ?
C13 C14A C15A C16A 179.8(10) . . . . ?
C14A C15A C16A N2A 0 . . . . ?
C15A C16A N2A C17A 0 . . . . ?
C16A N2A C17A C18A 0 . . . . ?
N2A C17A C18A C14A 0 . . . . ?
C15A C14A C18A C17A 0 . . . . ?
C13 C14A C18A C17A -179.8(10) . . . . ?
C18B C14B C15B C16B 0.0(3) . . . . ?
C20 C14B C15B C16B -178.8(5) . . . . ?
C14B C15B C16B N2B -0.8(3) . . . . ?
C15B C16B N2B C17B 0.7(3) . . . . ?
C16B N2B C17B C18B 0.2(3) . . . . ?
N2B C17B C18B C14B -1.0(3) . . . . ?
C15B C14B C18B C17B 0.8(3) . . . . ?
C20 C14B C18B C17B 179.6(5) . . . . ?
