#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558241.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_1558241
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            'C16.46 H14.46 N3.54 O2'
_chemical_formula_weight         293.85
_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             2020-03-12T16:24:37-00:00
_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                93.7189(12)
_cell_angle_beta                 106.5072(14)
_cell_angle_gamma                113.8224(14)
_cell_formula_units_Z            2
_cell_length_a                   7.98898(12)
_cell_length_b                   9.77584(13)
_cell_length_c                   10.85419(16)
_cell_measurement_reflns_used    14193
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      76.396
_cell_measurement_theta_min      4.309
_cell_volume                     727.76(2)
_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      230(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      -0.0288157
_diffrn_orient_matrix_UB_12      -0.16591
_diffrn_orient_matrix_UB_13      -0.0025372
_diffrn_orient_matrix_UB_21      -0.1022232
_diffrn_orient_matrix_UB_22      -0.0392667
_diffrn_orient_matrix_UB_23      -0.1499376
_diffrn_orient_matrix_UB_31      0.1973851
_diffrn_orient_matrix_UB_32      0.0436631
_diffrn_orient_matrix_UB_33      -0.019637
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0503
_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            27433
_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         77.316
_diffrn_reflns_theta_min         4.34
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.659
_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    1.341
_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         0.219
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035
_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   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2997
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0394
_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)+(0.0654P)²+0.0841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0
_reflns_number_gt                2686
_reflns_number_total             2997
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A75_BE25_230
_cod_database_code               1558241
_shelx_estimated_absorpt_t_min   0.854
_shelx_estimated_absorpt_t_max   0.959
_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 0.16517(12) 0.16059(10) 0.31159(8) 0.0487(2) Uani 1 1 d . . . . .
H1 H 0.197061 0.185901 0.392371 0.073 Uiso 1 1 calc R U . . .
O2 O 0.82309(13) 0.22373(11) 0.43419(9) 0.0568(3) Uani 1 1 d . . . . .
H2A H 0.82749 0.261963 0.50627 0.085 Uiso 1 1 calc R U . . .
N1 N 0.26054(15) 0.24909(12) 0.57922(10) 0.0485(3) Uani 1 1 d . . . . .
N2A N 0.2131(16) 0.3753(7) 0.9434(7) 0.0420(8) Uani 0.723(3) 1 d D U P A 1
N3A N 0.2686(10) 0.5138(6) 0.9819(4) 0.0410(6) Uani 0.723(3) 1 d D U P A 1
C17 C 0.214(6) 0.384(3) 0.937(3) 0.043(2) Uani 0.230(3) 1 d D U P A 2
H17 H 0.154695 0.303624 0.976564 0.052 Uiso 0.230(3) 1 calc R U P A 2
C18 C 0.260(4) 0.523(2) 0.9975(14) 0.0390(19) Uani 0.230(3) 1 d D U P A 2
H18 H 0.317247 0.604971 0.959234 0.047 Uiso 0.230(3) 1 calc DR U P A 2
N2B N 0.281(3) 0.473(3) 0.929(2) 0.045(3) Uani 0.047(2) 1 d D U P A 3
N3B N 0.190(3) 0.402(3) 0.997(2) 0.047(3) Uani 0.047(2) 1 d D U P A 3
N4 N 0.17589(14) 0.65020(12) 1.32797(9) 0.0464(3) Uani 1 1 d . . . . .
C1 C 0.31701(17) 0.15595(12) 0.28146(11) 0.0399(3) Uani 1 1 d . . . . .
C2 C 0.49342(17) 0.19032(12) 0.37765(10) 0.0411(3) Uani 1 1 d . . . . .
H2 H 0.509412 0.216248 0.466548 0.049 Uiso 1 1 calc R U . . .
C3 C 0.64697(18) 0.18662(13) 0.34321(11) 0.0433(3) Uani 1 1 d . . . . .
C4 C 0.6220(2) 0.14439(14) 0.21174(12) 0.0485(3) Uani 1 1 d . . . . .
H4 H 0.723642 0.139186 0.187582 0.058 Uiso 1 1 calc R U . . .
C5 C 0.4451(2) 0.11032(14) 0.11760(11) 0.0501(3) Uani 1 1 d . . . . .
H5 H 0.428323 0.082819 0.028767 0.06 Uiso 1 1 calc R U . . .
C6 C 0.29174(19) 0.11537(13) 0.14988(11) 0.0474(3) Uani 1 1 d . . . . .
H6 H 0.172682 0.091811 0.084068 0.057 Uiso 1 1 calc R U . . .
C7 C 0.32342(19) 0.39702(14) 0.62926(12) 0.0503(3) Uani 1 1 d . . . . .
H7 H 0.373193 0.469169 0.580068 0.06 Uiso 1 1 calc R U . . .
C8 C 0.31921(18) 0.44936(14) 0.74895(12) 0.0476(3) Uani 1 1 d . . . . .
H8 H 0.366886 0.55441 0.781121 0.057 Uiso 1 1 calc DR U . . .
C9 C 0.24258(16) 0.34258(13) 0.82061(11) 0.0417(3) Uani 1 1 d D . . . .
C10 C 0.18054(18) 0.18962(14) 0.77109(12) 0.0471(3) Uani 1 1 d . . . . .
H10 H 0.130914 0.114982 0.818383 0.057 Uiso 1 1 calc R U . . .
C11 C 0.19281(18) 0.14871(14) 0.65123(12) 0.0489(3) Uani 1 1 d . . . . .
H11 H 0.151295 0.044701 0.61856 0.059 Uiso 1 1 calc R U . . .
C12 C 0.23182(16) 0.55271(14) 1.10308(11) 0.0422(3) Uani 1 1 d D . . . .
C13 C 0.28739(19) 0.70491(14) 1.14686(12) 0.0495(3) Uani 1 1 d . . . . .
H13 H 0.344933 0.778213 1.100945 0.059 Uiso 1 1 calc R U . . .
C14 C 0.25758(19) 0.74836(14) 1.25877(13) 0.0507(3) Uani 1 1 d . . . . .
H14 H 0.296882 0.85277 1.287999 0.061 Uiso 1 1 calc R U . . .
C15 C 0.12096(18) 0.50194(14) 1.28495(12) 0.0465(3) Uani 1 1 d . . . . .
H15 H 0.06269 0.431246 1.332499 0.056 Uiso 1 1 calc R U . . .
C16 C 0.14600(18) 0.44789(14) 1.17368(12) 0.0465(3) Uani 1 1 d . . . . .
H16 H 0.106041 0.342988 1.146443 0.056 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 117.26(10) . . ?
N3A N2A C9 112.5(5) . . ?
N2A N3A C12 114.7(4) . . ?
C18 C17 C9 127.8(19) . . ?
C18 C17 H17 116.1 . . ?
C9 C17 H17 116.1 . . ?
C12 C18 C17 124.7(16) . . ?
C12 C18 H18 117.6 . . ?
C17 C18 H18 117.6 . . ?
N3B N2B C9 102(2) . . ?
N2B N3B C12 97(2) . . ?
C14 N4 C15 117.45(10) . . ?
O1 C1 C2 121.85(9) . . ?
O1 C1 C6 118.13(11) . . ?
C2 C1 C6 120.02(11) . . ?
C1 C2 C3 120.36(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.00(10) . . ?
O2 C3 C4 118.09(11) . . ?
C2 C3 C4 119.91(11) . . ?
C5 C4 C3 118.78(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.10(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.81(11) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.66(11) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.18(11) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 118.68(11) . . ?
C10 C9 C17 119.1(10) . . ?
C8 C9 C17 122.0(10) . . ?
C10 C9 N2A 115.4(3) . . ?
C8 C9 N2A 125.9(3) . . ?
C10 C9 N2B 151.6(8) . . ?
C8 C9 N2B 89.6(8) . . ?
C11 C10 C9 118.82(11) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.36(11) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C18 C12 C13 114.8(10) . . ?
C18 C12 C16 126.6(10) . . ?
C13 C12 C16 118.55(11) . . ?
C13 C12 N3A 116.3(2) . . ?
C16 C12 N3A 125.2(2) . . ?
C13 C12 N3B 155.2(7) . . ?
C16 C12 N3B 86.0(7) . . ?
C12 C13 C14 119.07(11) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
N4 C14 C13 123.46(11) . . ?
N4 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N4 C15 C16 123.07(11) . . ?
N4 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C15 C16 C12 118.41(11) . . ?
C15 C16 H16 120.8 . . ?
C12 C16 H16 120.8 . . ?
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(14) . ?
O1 H1 0.83 . ?
O2 C3 1.3558(15) . ?
O2 H2A 0.83 . ?
N1 C11 1.3333(17) . ?
N1 C7 1.3397(16) . ?
N2A N3A 1.241(4) . ?
N2A C9 1.455(5) . ?
N3A C12 1.485(3) . ?
C17 C18 1.320(10) . ?
C17 C9 1.412(19) . ?
C17 H17 0.94 . ?
C18 C12 1.266(9) . ?
C18 H18 0.94 . ?
N2B N3B 1.243(10) . ?
N2B C9 1.54(3) . ?
N3B C12 1.67(3) . ?
N4 C14 1.3331(17) . ?
N4 C15 1.3391(16) . ?
C1 C2 1.3874(16) . ?
C1 C6 1.3914(15) . ?
C2 C3 1.3931(17) . ?
C2 H2 0.94 . ?
C3 C4 1.3934(16) . ?
C4 C5 1.3807(19) . ?
C4 H4 0.94 . ?
C5 C6 1.3847(18) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3796(17) . ?
C7 H7 0.94 . ?
C8 C9 1.3889(17) . ?
C8 H8 0.94 . ?
C9 C10 1.3843(16) . ?
C10 C11 1.3779(17) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3753(17) . ?
C12 C16 1.3929(17) . ?
C13 C14 1.3754(18) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3848(17) . ?
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 2.7661(13) 176.8 . yes
O2 H2A N4 0.83 1.95 2.7840(13) 177.1 2_667 yes
