#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558205.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_1558205
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         290.93
_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             2020-04-02T10:38:48-00:00
_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                92.4662(11)
_cell_angle_beta                 108.0057(13)
_cell_angle_gamma                114.4642(14)
_cell_formula_units_Z            2
_cell_length_a                   8.21931(13)
_cell_length_b                   9.84133(13)
_cell_length_c                   10.95472(14)
_cell_measurement_reflns_used    9729
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      76.764
_cell_measurement_theta_min      4.312
_cell_volume                     751.94(2)
_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      270(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 0.969
_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      -0.1806034
_diffrn_orient_matrix_UB_12      -0.0487002
_diffrn_orient_matrix_UB_13      0.0357711
_diffrn_orient_matrix_UB_21      0.126618
_diffrn_orient_matrix_UB_22      0.0762334
_diffrn_orient_matrix_UB_23      0.1440904
_diffrn_orient_matrix_UB_31      -0.006865
_diffrn_orient_matrix_UB_32      0.1503187
_diffrn_orient_matrix_UB_33      -0.0266992
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.969
_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            14792
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.34
_diffrn_reflns_theta_min         4.329
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.90133
_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    1.285
_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         0.144
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0042(8)
_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   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     438
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0347
_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)+(0.0519P)²+0.0536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1016
_reflns_Friedel_coverage         0
_reflns_number_gt                2735
_reflns_number_total             3110
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE25_BA75_270
_cod_database_code               1558205
_shelx_estimated_absorpt_t_min   0.87
_shelx_estimated_absorpt_t_max   0.946
_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 0.16877(11) 0.14590(9) 0.30453(7) 0.0586(2) Uani 1 1 d . . . . .
H1 H 0.200784 0.170181 0.38399 0.088 Uiso 1 1 calc R U . . .
O2 O 0.81662(12) 0.21565(11) 0.43249(8) 0.0674(2) Uani 1 1 d . . . . .
H2A H 0.821508 0.250611 0.50357 0.101 Uiso 1 1 calc R U . . .
N1 N 0.26244(13) 0.24159(11) -0.43237(9) 0.0590(2) Uani 1 1 d . . . . .
C1 C 0.31854(15) 0.14617(10) 0.27609(9) 0.0477(2) Uani 1 1 d . . . . .
C2 C 0.49240(15) 0.17962(11) 0.37325(9) 0.0480(2) Uani 1 1 d . . . . .
H2 H 0.508239 0.201947 0.460745 0.058 Uiso 1 1 calc R U . . .
C3 C 0.64323(16) 0.17999(11) 0.34065(10) 0.0516(2) Uani 1 1 d . . . . .
C4 C 0.61840(18) 0.14347(13) 0.21000(11) 0.0607(3) Uani 1 1 d . . . . .
H4 H 0.71753 0.141456 0.187244 0.073 Uiso 1 1 calc R U . . .
C5 C 0.4448(2) 0.11034(14) 0.11493(11) 0.0647(3) Uani 1 1 d . . . . .
H5 H 0.428272 0.086434 0.027488 0.078 Uiso 1 1 calc R U . . .
C6 C 0.29430(18) 0.11157(12) 0.14558(10) 0.0590(3) Uani 1 1 d . . . . .
H6 H 0.178496 0.089511 0.079679 0.071 Uiso 1 1 calc R U . . .
C7 C 0.19737(16) 0.14745(13) -0.35624(11) 0.0579(3) Uani 1 1 d . . . . .
H7 H 0.15399 0.043791 -0.38388 0.069 Uiso 1 1 calc R U . . .
C8 C 0.19099(16) 0.19552(12) -0.23894(11) 0.0548(3) Uani 1 1 d . . . . .
H8 H 0.143164 0.125402 -0.189386 0.066 Uiso 1 1 calc R U . . .
C9 C 0.25665(14) 0.34976(12) -0.19525(10) 0.0493(2) Uani 1 1 d D . . . .
C10 C 0.32952(16) 0.44898(13) -0.27232(11) 0.0576(3) Uani 1 1 d . . . . .
H10 H 0.378606 0.553556 -0.24555 0.069 Uiso 1 1 calc R U . . .
C11 C 0.32789(17) 0.39007(14) -0.38876(12) 0.0615(3) Uani 1 1 d . . . . .
H11 H 0.375141 0.457516 -0.440327 0.074 Uiso 1 1 calc R U . . .
C12 C 0.220(2) 0.3831(11) -0.0691(13) 0.0436(16) Uani 0.306(12) 1 d D U P A 1
H12 H 0.163116 0.299875 -0.033668 0.052 Uiso 0.306(12) 1 calc R U P A 1
C13 C 0.2614(9) 0.5126(10) -0.0099(8) 0.0463(13) Uani 0.306(12) 1 d D U P A 1
H13 H 0.324828 0.59366 -0.04518 0.056 Uiso 0.306(12) 1 calc R U P A 1
C14A C 0.2242(19) 0.5581(13) 0.1096(10) 0.0431(19) Uani 0.306(12) 1 d DG U P A
1
C15A C 0.146(2) 0.4489(10) 0.1783(12) 0.053(2) Uani 0.306(12) 1 d G U P A 1
H15A H 0.113817 0.347559 0.150435 0.063 Uiso 0.306(12) 1 calc R U P A 1
C16A C 0.115(2) 0.4913(13) 0.2887(12) 0.050(2) Uani 0.306(12) 1 d G U P A 1
H16A H 0.062518 0.418313 0.334629 0.061 Uiso 0.306(12) 1 calc R U P A 1
N2A N 0.163(2) 0.6429(15) 0.3303(11) 0.048(2) Uani 0.306(12) 1 d G U P A 1
C17A C 0.241(2) 0.7520(11) 0.2616(11) 0.0490(19) Uani 0.306(12) 1 d G U P A 1
H17A H 0.273199 0.853388 0.289477 0.059 Uiso 0.306(12) 1 calc R U P A 1
C18A C 0.2720(18) 0.7096(11) 0.1513(10) 0.0482(19) Uani 0.306(12) 1 d G U P A 1
H18A H 0.324499 0.782636 0.105282 0.058 Uiso 0.306(12) 1 calc R U P A 1
C14B C 0.2158(9) 0.5265(7) 0.1229(5) 0.0479(9) Uani 0.694(12) 1 d D U P A 2
C15B C 0.1276(10) 0.4420(5) 0.2022(6) 0.0529(9) Uani 0.694(12) 1 d . U P A 2
H15B H 0.079061 0.336598 0.18639 0.064 Uiso 0.694(12) 1 calc R U P A 2
C16B C 0.1128(10) 0.5163(7) 0.3045(5) 0.0534(10) Uani 0.694(12) 1 d . U P A 2
H16B H 0.051818 0.457036 0.35572 0.064 Uiso 0.694(12) 1 calc R U P A 2
N2B N 0.1782(10) 0.6645(7) 0.3355(5) 0.0555(11) Uani 0.694(12) 1 d . U P A 2
C17B C 0.2620(10) 0.7425(6) 0.2596(6) 0.0580(11) Uani 0.694(12) 1 d . U P A 2
H17B H 0.311182 0.847857 0.279505 0.07 Uiso 0.694(12) 1 calc R U P A 2
C18B C 0.2833(8) 0.6827(6) 0.1541(5) 0.0520(9) Uani 0.694(12) 1 d . U P A 2
H18B H 0.342223 0.745789 0.104001 0.062 Uiso 0.694(12) 1 calc R U P A 2
C19 C 0.2535(10) 0.4148(7) -0.0799(6) 0.0557(11) Uani 0.694(12) 1 d D U P A 2
C20 C 0.2327(5) 0.4595(6) 0.0144(3) 0.0552(7) Uani 0.694(12) 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 6 -1 0.0431
-5 0 0 0.0431
1 -5 5 0.0478
5 0 0 0.0393
-1 -2 7 0.0812
2 -6 2 0.0449
0 3 -6 0.0824
0 5 -4 0.0552
5 -4 -4 0.0754
2 4 -1 0.0344
-3 -3 5 0.0681
5 -4 1 0.0424
3 0 4 0.0674
3 -4 4 0.0384
-3 -1 -4 0.0729
-1 1 7 0.0918
0 -3 -5 0.0753
3 -4 -5 0.0856
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 116.98(9) . . ?
O1 C1 C2 121.90(9) . . ?
O1 C1 C6 118.28(10) . . ?
C2 C1 C6 119.82(10) . . ?
C1 C2 C3 120.41(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 117.98(10) . . ?
O2 C3 C2 122.18(9) . . ?
C4 C3 C2 119.84(10) . . ?
C5 C4 C3 118.95(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.93(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.04(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.38(10) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.27(10) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 117.68(10) . . ?
C8 C9 C19 125.6(3) . . ?
C10 C9 C19 116.7(3) . . ?
C8 C9 C12 112.7(4) . . ?
C10 C9 C12 129.4(4) . . ?
C11 C10 C9 118.81(10) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.84(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 126.2(10) . . ?
C13 C12 H12 116.9 . . ?
C9 C12 H12 116.9 . . ?
C12 C13 C14A 130.8(11) . . ?
C12 C13 H13 114.6 . . ?
C14A C13 H13 114.6 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 120.2(6) . . ?
C18A C14A C13 119.8(6) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 116.2(2) . . ?
C18B C14B C20 121.0(4) . . ?
C15B C14B C20 122.8(3) . . ?
C16B C15B C14B 119.2(2) . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
N2B C16B C15B 125.0(2) . . ?
N2B C16B H16B 117.5 . . ?
C15B C16B H16B 117.5 . . ?
C17B N2B C16B 115.0(2) . . ?
N2B C17B C18B 125.8(3) . . ?
N2B C17B H17B 117.1 . . ?
C18B C17B H17B 117.1 . . ?
C17B C18B C14B 118.9(2) . . ?
C17B C18B H18B 120.6 . . ?
C14B C18B H18B 120.6 . . ?
C20 C19 C9 173.6(7) . . ?
C19 C20 C14B 174.4(7) . . ?
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(13) . ?
O1 H1 0.82 . ?
O2 C3 1.3548(13) . ?
O2 H2A 0.82 . ?
N1 C7 1.3310(15) . ?
N1 C11 1.3353(15) . ?
C1 C2 1.3868(15) . ?
C1 C6 1.3876(14) . ?
C2 C3 1.3909(15) . ?
C2 H2 0.93 . ?
C3 C4 1.3906(15) . ?
C4 C5 1.3759(18) . ?
C4 H4 0.93 . ?
C5 C6 1.3830(18) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3739(15) . ?
C7 H7 0.93 . ?
C8 C9 1.3870(15) . ?
C8 H8 0.93 . ?
C9 C10 1.3872(16) . ?
C9 C19 1.404(6) . ?
C9 C12 1.549(12) . ?
C10 C11 1.3721(16) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.264(12) . ?
C12 H12 0.93 . ?
C13 C14A 1.522(10) . ?
C13 H13 0.93 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.93 . ?
C16A N2A 1.39 . ?
C16A H16A 0.93 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.93 . ?
C18A H18A 0.93 . ?
C14B C18B 1.385(4) . ?
C14B C15B 1.387(4) . ?
C14B C20 1.405(5) . ?
C15B C16B 1.376(4) . ?
C15B H15B 0.93 . ?
C16B N2B 1.314(4) . ?
C16B H16B 0.93 . ?
N2B C17B 1.314(3) . ?
C17B C18B 1.366(3) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.193(7) . ?
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 0.82 1.94 2.7533(12) 173.7 1_556 yes
O2 H2A N2A^a 0.82 2 2.82(6) 173.7 2_666 yes
O2 H2A N2B^b 0.82 1.92 2.737(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 -179.52(9) . . . . ?
C6 C1 C2 C3 0.56(15) . . . . ?
C1 C2 C3 O2 178.38(9) . . . . ?
C1 C2 C3 C4 -1.36(15) . . . . ?
O2 C3 C4 C5 -178.50(10) . . . . ?
C2 C3 C4 C5 1.25(16) . . . . ?
C3 C4 C5 C6 -0.34(18) . . . . ?
C4 C5 C6 C1 -0.46(18) . . . . ?
O1 C1 C6 C5 -179.58(10) . . . . ?
C2 C1 C6 C5 0.35(15) . . . . ?
C11 N1 C7 C8 1.51(17) . . . . ?
N1 C7 C8 C9 -0.61(17) . . . . ?
C7 C8 C9 C10 -1.15(16) . . . . ?
C7 C8 C9 C19 177.9(4) . . . . ?
C7 C8 C9 C12 174.1(6) . . . . ?
C8 C9 C10 C11 1.91(16) . . . . ?
C19 C9 C10 C11 -177.2(4) . . . . ?
C12 C9 C10 C11 -172.4(8) . . . . ?
C7 N1 C11 C10 -0.67(17) . . . . ?
C9 C10 C11 N1 -1.05(18) . . . . ?
C8 C9 C12 C13 -178.3(11) . . . . ?
C10 C9 C12 C13 -3.7(18) . . . . ?
C9 C12 C13 C14A 176.6(10) . . . . ?
C12 C13 C14A C15A 5.7(15) . . . . ?
C12 C13 C14A C18A -175.4(12) . . . . ?
C18A C14A C15A C16A 0 . . . . ?
C13 C14A C15A C16A 178.9(11) . . . . ?
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 -178.9(11) . . . . ?
C18B C14B C15B C16B -0.1(3) . . . . ?
C20 C14B C15B C16B -178.4(5) . . . . ?
C14B C15B C16B N2B -0.7(3) . . . . ?
C15B C16B N2B C17B 0.4(3) . . . . ?
C16B N2B C17B C18B 0.7(4) . . . . ?
N2B C17B C18B C14B -1.4(4) . . . . ?
C15B C14B C18B C17B 1.0(3) . . . . ?
C20 C14B C18B C17B 179.3(5) . . . . ?
