#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558250.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_1558250
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            'C16.45 H14.45 N3.55 O2'
_chemical_formula_weight         293.87
_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             2020-03-12T16:25:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                93.8151(16)
_cell_angle_beta                 106.4802(19)
_cell_angle_gamma                113.764(2)
_cell_formula_units_Z            2
_cell_length_a                   8.00509(19)
_cell_length_b                   9.78356(18)
_cell_length_c                   10.8603(2)
_cell_measurement_reflns_used    13463
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      76.361
_cell_measurement_theta_min      4.323
_cell_volume                     730.44(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_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      -0.0285982
_diffrn_orient_matrix_UB_12      -0.165702
_diffrn_orient_matrix_UB_13      -0.0023322
_diffrn_orient_matrix_UB_21      -0.1009774
_diffrn_orient_matrix_UB_22      -0.0394227
_diffrn_orient_matrix_UB_23      -0.1499787
_diffrn_orient_matrix_UB_31      0.1974381
_diffrn_orient_matrix_UB_32      0.043628
_diffrn_orient_matrix_UB_33      -0.0188307
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27550
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.243
_diffrn_reflns_theta_min         4.338
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0049(10)
_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   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3003
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0412
_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)+(0.0664P)²+0.0905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.116
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0
_reflns_number_gt                2641
_reflns_number_total             3003
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A75_BE25_250
_cod_database_code               1558250
_shelx_estimated_absorpt_t_min   0.854
_shelx_estimated_absorpt_t_max   0.96
_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 0.16557(13) 0.15964(11) 0.31162(8) 0.0534(3) Uani 1 1 d . . . . .
H1 H 0.197807 0.186395 0.392255 0.08 Uiso 1 1 calc R U . . .
O2 O 0.82228(14) 0.22356(12) 0.43391(9) 0.0624(3) Uani 1 1 d . . . . .
H2A H 0.826747 0.261792 0.506027 0.094 Uiso 1 1 calc R U . . .
N1 N 0.26025(16) 0.24892(13) 0.57924(10) 0.0526(3) Uani 1 1 d . . . . .
N2A N 0.2136(19) 0.3763(7) 0.9430(8) 0.0458(9) Uani 0.707(3) 1 d D U P A 1
N3A N 0.2685(11) 0.5145(7) 0.9820(5) 0.0445(6) Uani 0.707(3) 1 d D U P A 1
C17 C 0.213(7) 0.381(3) 0.938(3) 0.047(3) Uani 0.225(3) 1 d D U P A 2
H17 H 0.155989 0.299639 0.976944 0.057 Uiso 0.225(3) 1 calc R U P A 2
C18 C 0.258(4) 0.519(3) 0.9978(17) 0.045(2) Uani 0.225(3) 1 d D U P A 2
H18 H 0.314616 0.600753 0.958757 0.054 Uiso 0.225(3) 1 calc DR U P A 2
N2B N 0.281(3) 0.475(2) 0.9293(17) 0.049(3) Uani 0.068(2) 1 d D U P A 3
N3B N 0.188(2) 0.403(2) 0.9964(17) 0.050(2) Uani 0.068(2) 1 d D U P A 3
N4 N 0.17640(15) 0.65015(12) 1.32797(10) 0.0504(3) Uani 1 1 d . . . . .
C1 C 0.31736(18) 0.15526(12) 0.28167(11) 0.0436(3) Uani 1 1 d . . . . .
C2 C 0.49305(18) 0.18963(13) 0.37755(11) 0.0448(3) Uani 1 1 d . . . . .
H2 H 0.508949 0.215435 0.466428 0.054 Uiso 1 1 calc R U . . .
C3 C 0.64631(19) 0.18621(13) 0.34311(12) 0.0473(3) Uani 1 1 d . . . . .
C4 C 0.6211(2) 0.14410(14) 0.21168(13) 0.0530(3) Uani 1 1 d . . . . .
H4 H 0.722579 0.138936 0.187475 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4452(2) 0.11014(15) 0.11768(12) 0.0549(3) Uani 1 1 d . . . . .
H5 H 0.428557 0.082902 0.028861 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2922(2) 0.11493(14) 0.15008(12) 0.0517(3) Uani 1 1 d . . . . .
H6 H 0.173394 0.091336 0.084361 0.062 Uiso 1 1 calc R U . . .
C7 C 0.3233(2) 0.39660(15) 0.62908(13) 0.0549(3) Uani 1 1 d . . . . .
H7 H 0.373026 0.46841 0.579833 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3194(2) 0.44948(15) 0.74871(13) 0.0525(3) Uani 1 1 d . . . . .
H8 H 0.367145 0.554513 0.780784 0.063 Uiso 1 1 calc DR U . . .
C9 C 0.24290(17) 0.34322(14) 0.82035(11) 0.0458(3) Uani 1 1 d D . . . .
C10 C 0.18111(19) 0.19064(15) 0.77114(13) 0.0517(3) Uani 1 1 d . . . . .
H10 H 0.131886 0.116364 0.818623 0.062 Uiso 1 1 calc R U . . .
C11 C 0.1928(2) 0.14918(15) 0.65140(13) 0.0533(3) Uani 1 1 d . . . . .
H11 H 0.151117 0.045149 0.618863 0.064 Uiso 1 1 calc R U . . .
C12 C 0.23152(18) 0.55207(15) 1.10325(11) 0.0467(3) Uani 1 1 d D . . . .
C13 C 0.2867(2) 0.70374(15) 1.14685(13) 0.0544(3) Uani 1 1 d . . . . .
H13 H 0.343717 0.776734 1.100738 0.065 Uiso 1 1 calc R U . . .
C14 C 0.2578(2) 0.74759(15) 1.25864(13) 0.0555(3) Uani 1 1 d . . . . .
H14 H 0.29746 0.852027 1.287852 0.067 Uiso 1 1 calc R U . . .
C15 C 0.12132(19) 0.50218(15) 1.28518(12) 0.0511(3) Uani 1 1 d . . . . .
H15 H 0.063113 0.431858 1.332797 0.061 Uiso 1 1 calc R U . . .
C16 C 0.1460(2) 0.44758(15) 1.17389(13) 0.0516(3) Uani 1 1 d . . . . .
H16 H 0.106101 0.342717 1.146758 0.062 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 0.0181 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
-1 6 -1 0.055
0 4 4 0.0525
0 -6 2 0.0757
3 -6 0 0.0674
5 -1 0 0.0887
5 0 -3 0.0947
0 0 7 0.026
0 0 -7 0.0283
-2 -3 -2 0.0761
-5 0 3 0.0919
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 . . ?
C11 N1 C7 117.21(11) . . ?
N3A N2A C9 112.9(5) . . ?
N2A N3A C12 114.5(4) . . ?
C18 C17 C9 126.2(19) . . ?
C18 C17 H17 116.9 . . ?
C9 C17 H17 116.9 . . ?
C12 C18 C17 125.8(17) . . ?
C12 C18 H18 117.1 . . ?
C17 C18 H18 117.1 . . ?
N3B N2B C9 101.3(18) . . ?
N2B N3B C12 97.0(16) . . ?
C14 N4 C15 117.41(11) . . ?
O1 C1 C2 121.97(10) . . ?
O1 C1 C6 118.01(11) . . ?
C2 C1 C6 120.02(11) . . ?
C1 C2 C3 120.39(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.09(10) . . ?
O2 C3 C4 118.11(11) . . ?
C2 C3 C4 119.79(12) . . ?
C5 C4 C3 118.95(12) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.98(11) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.84(12) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.69(12) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.12(12) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 118.69(11) . . ?
C10 C9 C17 117.5(11) . . ?
C8 C9 C17 123.7(11) . . ?
C10 C9 N2A 115.4(3) . . ?
C8 C9 N2A 125.9(3) . . ?
C10 C9 N2B 151.5(6) . . ?
C8 C9 N2B 89.8(6) . . ?
C11 C10 C9 118.87(12) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.37(12) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C18 C12 C13 115.8(11) . . ?
C18 C12 C16 125.6(11) . . ?
C13 C12 C16 118.54(12) . . ?
C13 C12 N3A 115.7(3) . . ?
C16 C12 N3A 125.7(3) . . ?
C13 C12 N3B 154.7(5) . . ?
C16 C12 N3B 86.4(5) . . ?
C12 C13 C14 119.16(12) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N4 C14 C13 123.52(12) . . ?
N4 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N4 C15 C16 123.06(12) . . ?
N4 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C15 C16 C12 118.30(12) . . ?
C15 C16 H16 120.9 . . ?
C12 C16 H16 120.9 . . ?
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 1.3595(15) . ?
O1 H1 0.83 . ?
O2 C3 1.3562(16) . ?
O2 H2A 0.83 . ?
N1 C11 1.3323(18) . ?
N1 C7 1.3374(17) . ?
N2A N3A 1.240(4) . ?
N2A C9 1.455(5) . ?
N3A C12 1.483(3) . ?
C17 C18 1.321(10) . ?
C17 C9 1.414(19) . ?
C17 H17 0.94 . ?
C18 C12 1.265(9) . ?
C18 H18 0.94 . ?
N2B N3B 1.242(10) . ?
N2B C9 1.56(2) . ?
N3B C12 1.65(2) . ?
N4 C14 1.3317(18) . ?
N4 C15 1.3364(17) . ?
C1 C2 1.3845(17) . ?
C1 C6 1.3915(16) . ?
C2 C3 1.3921(17) . ?
C2 H2 0.94 . ?
C3 C4 1.3926(17) . ?
C4 C5 1.378(2) . ?
C4 H4 0.94 . ?
C5 C6 1.383(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3795(18) . ?
C7 H7 0.94 . ?
C8 C9 1.3878(19) . ?
C8 H8 0.94 . ?
C9 C10 1.3811(17) . ?
C10 C11 1.3762(18) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3714(19) . ?
C12 C16 1.3930(19) . ?
C13 C14 1.3720(19) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3856(18) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?
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 0.83 1.94 2.7684(14) 177.1 . yes
O2 H2A N4 0.83 1.96 2.7862(14) 177.1 2_667 yes
