#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558246.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_1558246
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            'C16.59 H14.59 N3.41 O2'
_chemical_formula_weight         293.73
_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             2020-03-12T16:23:52-00:00
_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                93.6260(17)
_cell_angle_beta                 106.527(2)
_cell_angle_gamma                113.856(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9687(2)
_cell_length_b                   9.7664(2)
_cell_length_c                   10.8474(2)
_cell_measurement_reflns_used    14876
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      76.711
_cell_measurement_theta_min      4.302
_cell_volume                     724.72(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      210(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 0.971
_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      -0.0286176
_diffrn_orient_matrix_UB_12      -0.1659892
_diffrn_orient_matrix_UB_13      -0.0022722
_diffrn_orient_matrix_UB_21      -0.1030492
_diffrn_orient_matrix_UB_22      -0.0394921
_diffrn_orient_matrix_UB_23      -0.1499495
_diffrn_orient_matrix_UB_31      0.1976735
_diffrn_orient_matrix_UB_32      0.0438129
_diffrn_orient_matrix_UB_33      -0.0200628
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_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            27317
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.219
_diffrn_reflns_theta_min         4.342
_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    1.346
_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         0.237
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0047(9)
_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   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.0388
_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)+(0.0622P)²+0.1035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0
_reflns_number_gt                2703
_reflns_number_total             2988
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A75_BE25_210
_cod_original_cell_volume        724.71(3)
_cod_database_code               1558246
_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 0.16492(12) 0.16133(10) 0.31161(8) 0.0444(2) Uani 1 1 d . . . . .
H1 H 0.197213 0.187151 0.392392 0.067 Uiso 1 1 calc R U . . .
O2 O 0.82413(13) 0.22402(11) 0.43440(8) 0.0516(3) Uani 1 1 d . . . . .
H2A H 0.829046 0.263434 0.506204 0.077 Uiso 1 1 calc R U . . .
N1 N 0.26075(15) 0.24927(12) 0.57928(10) 0.0445(3) Uani 1 1 d . . . . .
N2A N 0.2133(16) 0.3754(7) 0.9437(7) 0.0382(9) Uani 0.723(3) 1 d D U P A 1
N3A N 0.2683(10) 0.5143(6) 0.9814(4) 0.0368(6) Uani 0.723(3) 1 d D U P A 1
C17 C 0.213(6) 0.383(2) 0.937(3) 0.039(2) Uani 0.243(3) 1 d D U P A 2
H17 H 0.150579 0.30118 0.97482 0.047 Uiso 0.243(3) 1 calc R U P A 2
C18 C 0.263(4) 0.521(2) 0.9995(14) 0.0367(19) Uani 0.243(3) 1 d D U P A 2
H18 H 0.326532 0.603621 0.963343 0.044 Uiso 0.243(3) 1 calc DR U P A 2
N2B N 0.286(5) 0.477(4) 0.932(3) 0.041(3) Uani 0.034(2) 1 d D U P A 3
N3B N 0.186(4) 0.404(4) 0.996(3) 0.042(3) Uani 0.034(2) 1 d D U P A 3
N4 N 0.17550(14) 0.65025(11) 1.32807(9) 0.0425(2) Uani 1 1 d . . . . .
C1 C 0.31682(17) 0.15645(12) 0.28143(11) 0.0369(3) Uani 1 1 d . . . . .
C2 C 0.49365(17) 0.19092(12) 0.37764(10) 0.0377(3) Uani 1 1 d . . . . .
H2 H 0.509802 0.217151 0.466543 0.045 Uiso 1 1 calc R U . . .
C3 C 0.64751(17) 0.18688(12) 0.34325(11) 0.0394(3) Uani 1 1 d . . . . .
C4 C 0.62221(19) 0.14460(13) 0.21165(12) 0.0444(3) Uani 1 1 d . . . . .
H4 H 0.724165 0.139412 0.187537 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4450(2) 0.11045(13) 0.11729(11) 0.0457(3) Uani 1 1 d . . . . .
H5 H 0.428164 0.082791 0.028461 0.055 Uiso 1 1 calc R U . . .
C6 C 0.29143(19) 0.11573(13) 0.14961(11) 0.0435(3) Uani 1 1 d . . . . .
H6 H 0.172074 0.092258 0.083781 0.052 Uiso 1 1 calc R U . . .
C7 C 0.32370(18) 0.39730(14) 0.62954(12) 0.0461(3) Uani 1 1 d . . . . .
H7 H 0.373756 0.469724 0.580426 0.055 Uiso 1 1 calc R U . . .
C8 C 0.31923(18) 0.44942(14) 0.74914(12) 0.0434(3) Uani 1 1 d . . . . .
H8 H 0.366885 0.554511 0.781367 0.052 Uiso 1 1 calc DR U . . .
C9 C 0.24216(16) 0.34200(13) 0.82071(11) 0.0374(3) Uani 1 1 d D . . . .
C10 C 0.18019(18) 0.18889(14) 0.77110(12) 0.0427(3) Uani 1 1 d . . . . .
H10 H 0.130473 0.113982 0.818367 0.051 Uiso 1 1 calc R U . . .
C11 C 0.19276(18) 0.14839(14) 0.65117(12) 0.0446(3) Uani 1 1 d . . . . .
H11 H 0.1513 0.044372 0.618392 0.053 Uiso 1 1 calc R U . . .
C12 C 0.23214(16) 0.55308(13) 1.10292(11) 0.0381(3) Uani 1 1 d D . . . .
C13 C 0.28780(18) 0.70584(14) 1.14686(12) 0.0448(3) Uani 1 1 d . . . . .
H13 H 0.345552 0.779395 1.100983 0.054 Uiso 1 1 calc R U . . .
C14 C 0.25751(18) 0.74898(14) 1.25890(12) 0.0463(3) Uani 1 1 d . . . . .
H14 H 0.296651 0.85341 1.288153 0.056 Uiso 1 1 calc R U . . .
C15 C 0.12061(17) 0.50177(14) 1.28468(12) 0.0424(3) Uani 1 1 d . . . . .
H15 H 0.062067 0.430742 1.332119 0.051 Uiso 1 1 calc R U . . .
C16 C 0.14591(18) 0.44808(13) 1.17361(12) 0.0421(3) Uani 1 1 d . . . . .
H16 H 0.105838 0.343102 1.14639 0.051 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 117.27(10) . . ?
N3A N2A C9 112.5(5) . . ?
N2A N3A C12 114.5(4) . . ?
C18 C17 C9 127.8(18) . . ?
C18 C17 H17 116.1 . . ?
C9 C17 H17 116.1 . . ?
C12 C18 C17 126.1(17) . . ?
C12 C18 H18 117 . . ?
C17 C18 H18 117 . . ?
N3B N2B C9 100(3) . . ?
N2B N3B C12 96(3) . . ?
C14 N4 C15 117.38(10) . . ?
O1 C1 C2 121.79(9) . . ?
O1 C1 C6 118.18(10) . . ?
C2 C1 C6 120.03(11) . . ?
C1 C2 C3 120.36(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 121.96(10) . . ?
O2 C3 C4 118.20(11) . . ?
C2 C3 C4 119.84(11) . . ?
C5 C4 C3 118.95(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.96(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.85(11) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.76(11) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.06(11) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C10 C9 C8 118.74(11) . . ?
C10 C9 C17 118.9(10) . . ?
C8 C9 C17 122.2(10) . . ?
C10 C9 N2A 115.8(3) . . ?
C8 C9 N2A 125.5(3) . . ?
C10 C9 N2B 152.1(10) . . ?
C8 C9 N2B 89.1(10) . . ?
C11 C10 C9 118.79(11) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.34(11) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C18 C12 C13 115.9(10) . . ?
C18 C12 C16 125.7(10) . . ?
C13 C12 C16 118.44(11) . . ?
C13 C12 N3A 116.3(2) . . ?
C16 C12 N3A 125.2(2) . . ?
C13 C12 N3B 154.8(9) . . ?
C16 C12 N3B 86.2(9) . . ?
C14 C13 C12 119.05(11) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N4 C14 C13 123.41(11) . . ?
N4 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N4 C15 C16 123.21(11) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.50(11) . . ?
C15 C16 H16 120.7 . . ?
C12 C16 H16 120.7 . . ?
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 1.3583(14) . ?
O1 H1 0.83 . ?
O2 C3 1.3564(14) . ?
O2 H2A 0.83 . ?
N1 C11 1.3335(16) . ?
N1 C7 1.3405(16) . ?
N2A N3A 1.244(4) . ?
N2A C9 1.456(5) . ?
N3A C12 1.484(3) . ?
C17 C18 1.322(10) . ?
C17 C9 1.408(18) . ?
C17 H17 0.94 . ?
C18 C12 1.260(9) . ?
C18 H18 0.94 . ?
N2B N3B 1.242(10) . ?
N2B C9 1.58(4) . ?
N3B C12 1.65(4) . ?
N4 C14 1.3344(16) . ?
N4 C15 1.3413(15) . ?
C1 C2 1.3868(16) . ?
C1 C6 1.3936(15) . ?
C2 C3 1.3934(16) . ?
C2 H2 0.94 . ?
C3 C4 1.3940(16) . ?
C4 C5 1.3807(18) . ?
C4 H4 0.94 . ?
C5 C6 1.3843(18) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3788(17) . ?
C7 H7 0.94 . ?
C8 C9 1.3905(17) . ?
C8 H8 0.94 . ?
C9 C10 1.3853(16) . ?
C10 C11 1.3785(16) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3799(17) . ?
C12 C16 1.3931(17) . ?
C13 C14 1.3774(17) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3824(16) . ?
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 2.7647(13) 177 . yes
O2 H2A N4 0.83 1.95 2.7820(13) 176.7 2_667 yes
